Details of the Researcher

PHOTO

Azusa Kondoh
Section
Graduate School of Science
Job title
Associate Professor
Degree
e-Rad No.
30645544

Research History 3

  • 2014/06 - 2020/03
    Tohoku University Research and Analytical Center for Giant Molecules, Graduate School of Science

  • 2012/04 - 2014/05
    東北大学

  • 2010/04 - 2012/03
    マックスプランク石炭研究所 博士研究員

Education 2

  • 京都大学大学院 工学研究科 材料化学専攻

    2005/04 - 2010/03

  • Kyoto University Faculty of Engineering School of Industrial Chemistry

    2001/04 - 2005/03

Professional Memberships 4

  • The Kinka Chemical Society, Japan

  • アメリカ化学会

  • THE SOCIETY OF SYNTHETIC ORGANIC CHEMISTRY, JAPAN

  • THE CHEMICAL SOCIETY OF JAPAN

Research Interests 3

  • 有機分子触媒

  • 有機金属化学

  • 有機合成化学

Research Areas 1

  • Nanotechnology/Materials / Synthetic organic chemistry /

Awards 9

  1. 2022 Asian Core Program Lectureship Award (South Korea & Taiwan)

    2022/07 Chiral Ureates as Chiral Strong Brønsted Base Catalysts

  2. 第21回グリーン・サステイナブル ケミストリー(GSC)賞 奨励賞

    2022/06 公益社団法人 新化学技術推進協会 不斉有機超強塩基触媒を用いた不斉分子変換反応の開発

  3. Thieme Journals Award 2021

    2020/12 Thieme Chemistry

  4. Chemist Award BCA 2020

    2020/10 公益財団法人MSD生命科学財団 有機超強塩基によるアニオンの触媒的発生を鍵とする分子変換反応の開発

  5. 東北大学ディスティングイッシュトリサーチャー

    2020/05 東北大学

  6. 令和2年度科学技術分野の文部科学大臣表彰 若手科学者賞

    2020/04 文部科学省 有機超強塩基による触媒的分子変換反応の開発に関する研究

  7. 第68回進歩賞

    2019/03 日本化学会 有機超強塩基によるアニオンの触媒的発生を鍵とする分子変換反応の開発

  8. 第31回若い世代の特別講演会

    2017/03 日本化学会 強塩基性ブレンステッド塩基触媒が拓く新たな炭素-炭素結合生成反応

  9. 日産化学工業 研究企画賞

    2015/02 有機合成化学協会

Show all ︎Show 5

Papers 91

  1. Brønsted Base-Catalyzed Aminoxylation of Benzylic and Allylic Compounds with TEMPO Peer-reviewed

    Azusa Kondoh, Masahiro Terada

    Organic Letters 2026/02/20

    DOI: 10.1021/acs.orglett.6c00102  

  2. Modular Synthesis of 2,3,4,6‐Tetrasubstituted Thieno[2,3‐c]furans Based on Formal [3+2] Cycloaddition Utilizing [1,2]‐Phospha‐Brook Rearrangement / Brønsted Base‐Mediated Cyclization Strategy Peer-reviewed

    Azusa Kondoh, Kohei Aita, Masahiro Terada

    Advanced Synthesis & Catalysis 2025/05/20

    DOI: 10.1002/adsc.202500255  

  3. Asymmetric Construction of Acyclic 1,3‐Nonadjacent Stereogenic Centers Containing a Tetrasubstituted Carbon through Diastereoselective Alkylation of Benzyl Sulfone Derivatives Peer-reviewed

    Rihaku Ojima, Azusa Kondoh, Masahiro Terada

    European Journal of Organic Chemistry 2025/03/10

    DOI: 10.1002/ejoc.202401292  

  4. Phosphazene base-catalyzed telescopic three-component reaction involving 1,1-difunctionalization of electron-deficient alkenes Peer-reviewed

    Azusa Kondoh, Sho Yamaguchi, Masahiro Terada

    Chemical Communications 2025

    DOI: 10.1039/D4CC05169F  

  5. Catalytic Generation of Benzyl Anions from Aryl Ketones Utilizing [1,2]‐Phospha‐Brook Rearrangement and Their Application to Synthesis of Tertiary Benzylic Alcohols Peer-reviewed

    Azusa Kondoh, Hirochika Suzuki, Takayuki Hirozane, Masahiro Terada

    Chemistry – A European Journal 2024/12/10

    DOI: 10.1002/chem.202402967  

  6. Asymmetric Auto-Tandem Catalysis with Chiral Organosuperbases: Intramolecular Cyclization/Enantioselective Direct Mannich-Type Addition Sequence Peer-reviewed

    Azusa Kondoh, Takuro Kato, Hao Chen, Masahiro Terada

    Organic Letters 2024/08/02

    DOI: 10.1021/acs.orglett.4c02532  

  7. Catalytic Generation and Intermolecular Addition of Diarylmethyl Anions Utilizing [1,2]‐Phospha‐Brook Rearrangement Under Brønsted Base Catalysis Peer-reviewed

    Azusa Kondoh, Masahiro Terada

    Advanced Synthesis & Catalysis 366 (8) 1857-1862 2024/03/05

    Publisher: Wiley

    DOI: 10.1002/adsc.202301503  

    ISSN: 1615-4150

    eISSN: 1615-4169

    More details Close

    Abstract An intermolecular addition reaction involving an unconventional combination of a diarylmethyl anion and an electrophile, which is mediated by the [1,2]‐phospha‐Brook rearrangement under Brønsted base catalysis, was developed. Diarylmethyl anions having a benzofuran moiety were generated through the rearrangement with the aid of a catalytic amount of phosphazene base P2‐tBu. The resulting carbanion intermediates were trapped by various electrophiles, such as α,β‐unsaturated ketones, aryl aldehydes, α‐ketoesters, and N‐Boc imines, providing the corresponding diarylalkane derivatives in good yields.

  8. Construction of 1,3‐Nonadjacent Stereogenic Centers Through Enantioselective Addition of α‐Thioacetamides to α‐Substituted Vinyl Sulfones Catalyzed by Chiral Strong Brønsted Base Peer-reviewed

    Azusa Kondoh, Rihaku Ojima, Sho Ishikawa, Masahiro Terada

    Advanced Science 2024/03

    DOI: 10.1002/advs.202308020  

  9. Brønsted Base-Catalyzed Reductive Deimination of α-Iminoketones Peer-reviewed

    Azusa Kondoh, Seitaro Inoue, Rihaku Ojima, Masahiro Terada

    Bulletin of the Chemical Society of Japan 96 (9) 849-851 2023/07/25

    Publisher: Oxford University Press (OUP)

    DOI: 10.1246/bcsj.20230125  

    ISSN: 0009-2673

    eISSN: 1348-0634

    More details Close

    Abstract An unprecedented reductive deimination of α-iminoketones derived from benzils was developed under Brønsted base catalysis. Treatment of α-iminoketones with silanethiols in the presence of a catalytic amount of P2-tBu provided the corresponding arylbenzylketones in good yields. This is a rare example of the direct transformation of an imine moiety into a methylene moiety.

  10. Formal Addition of β‐Acylalkenyl Anions to Ketones Utilizing [1,2]‐Phospha‐Brook Rearrangement under Brønsted Base Catalysis Peer-reviewed

    Azusa Kondoh, Sena Takada, Kohei Aita, Masahiro Terada

    European Journal of Organic Chemistry 2023/07/03

    DOI: 10.1002/ejoc.202300425  

  11. Synthesis of Polysubstituted Naphthofurans and Indenofurans Based on a Regiodivergent Intramolecular Carbometalation Strategy with 2‐(2’‐Alkynylaryl)‐3‐iodofurans Peer-reviewed

    Azusa Kondoh, Kohei Aita, Masahiro Terada

    Chemistry – A European Journal 2023/05/02

    DOI: 10.1002/chem.202300132  

  12. [1,2]‐Phospha‐Brook Rearrangement as Tool for Generation of Anionic Nucleophiles in Addition Reactions under Brønsted Base Catalysis Peer-reviewed

    Azusa Kondoh, Masahiro Terada

    Asian Journal of Organic Chemistry 2023/03

    DOI: 10.1002/ajoc.202300003  

  13. Enantioselective direct Michael addition of cyanohydrin ether derivatives to enones catalyzed by chiral bis(guanidino)iminophosphorane organosuperbase Peer-reviewed

    Saikat Das, Azusa Kondoh, Masahiro Terada

    Chemical Science 2023

    DOI: 10.1039/D2SC07065K  

  14. Brønsted Base Catalyzed Conjugate Addition of β-Acylvinyl Anion Equivalents to α,β-Unsaturated Ketones Peer-reviewed

    Azusa Kondoh, Masahiro Terada, Sho Yamaguchi, Yushi Watanabe

    Synlett 2022/11

    Publisher: Georg Thieme Verlag {KG}

    DOI: 10.1055/a-1827-5652  

  15. Synthesis of 2,2‐Disubstituted 2H‐Chromenes through Carbon‐Carbon Bond Formation Utilizing a [1,2]‐Phospha‐Brook Rearrangement under Brønsted Base Catalysis Peer-reviewed

    Azusa Kondoh, Masahiro Terada

    Chemistry – A European Journal 2022/08/10

    DOI: 10.1002/chem.202201198  

  16. Formal Umpolung Addition of Phosphites to 2‐Azaaryl Ketones under Chiral Brønsted Base Catalysis: Enantioselective Protonation Utilizing [1,2]‐Phospha‐Brook Rearrangement Peer-reviewed

    Azusa Kondoh, Takayuki Hirozane, Masahiro Terada

    Chemistry – A European Journal 2022/07/26

    DOI: 10.1002/chem.202201240  

  17. Brønsted base-catalyzed 1,2-addition/[1,2]-phospha-Brook rearrangement sequence providing functionalized phosphonates Peer-reviewed

    Azusa Kondoh, Masahiro Terada

    Organic & Biomolecular Chemistry 20 (14) 2863-2866 2022

    Publisher: Royal Society of Chemistry ({RSC})

    DOI: 10.1039/D2OB00256F  

  18. Formal Fluorinative Ring Opening of 2-Benzoylpyrrolidines Utilizing [1,2]-Phospha-Brook Rearrangement for Synthesis of 2-Aryl-3-fluoropiperidines Peer-reviewed

    Azusa Kondoh, Rihaku Ojima, Masahiro Terada

    Organic Letters 23 (20) 7894-7899 2021/10/15

    Publisher: American Chemical Society ({ACS})

    DOI: 10.1021/acs.orglett.1c02907  

  19. Enantioselective Protonation: Hydrophosphinylation of 1,1‐Vinyl Azaheterocycle N‐Oxides Catalyzed by Chiral Bis(guanidino)iminophosphorane Organosuperbase

    Saikat Das, Qiupeng Hu, Azusa Kondoh, Masahiro Terada

    Angewandte Chemie 133 (3) 1437-1442 2021/01/18

    Publisher: Wiley

    DOI: 10.1002/ange.202012492  

  20. Enantioselective Protonation through Hydrophosphinylation of 1,1‐Vinyl Azaheterocycle N‐Oxides Catalyzed by Chiral Bis(guanidino)iminophosphorane as Higher Order Organosuperbase Peer-reviewed

    Saikat Das, Qiupeng Hu, Azusa Kondoh, Masahiro Terada

    Angewandte Chemie International Edition 60 (3) 1417-1422 2020/10/08

    Publisher: Wiley

    DOI: 10.1002/anie.202012492  

    ISSN: 1433-7851

    eISSN: 1521-3773

  21. Brønsted Base‐Catalyzed Formal Reductive [3+2] Annulation of 4,4,4‐Trifluorocrotonate and α‐Iminoketones Peer-reviewed

    Azusa Kondoh, Masahiro Terada

    Chemistry – A European Journal 27 (2) 585-588 2020/09

    Publisher: Wiley

    DOI: 10.1002/chem.202002943  

    ISSN: 0947-6539

    eISSN: 1521-3765

  22. Brønsted Base-Catalyzed Transformation of α,β-Epoxyketones Utilizing [1,2]-Phospha-Brook Rearrangement for the Synthesis of Allylic Alcohols Having a Tetrasubstituted Alkene Moiety Peer-reviewed

    Azusa Kondoh, Naoko Tasato, Takuma Aoki, Masahiro Terada

    Organic Letters 22 (13) 5170-5175 2020/07/02

    Publisher: American Chemical Society ({ACS})

    DOI: 10.1021/acs.orglett.0c01765  

    ISSN: 1523-7060

    eISSN: 1523-7052

  23. Frontispiz: Development of Chiral Organosuperbase Catalysts Consisting of Two Different Organobase Functionalities Peer-reviewed

    Azusa Kondoh, Masafumi Oishi, Hikaru Tezuka, Masahiro Terada

    Angewandte Chemie 132 (19) 7542-7547 2020/05/04

    Publisher: Wiley

    DOI: 10.1002/ange.202081962  

  24. Frontispiece: Development of Chiral Organosuperbase Catalysts Consisting of Two Different Organobase Functionalities Peer-reviewed

    Azusa Kondoh, Masafumi Oishi, Hikaru Tezuka, Masahiro Terada

    Angewandte Chemie International Edition 59 (19) 7472-7477 2020/05/04

    Publisher: Wiley

    DOI: 10.1002/anie.202081962  

    ISSN: 1433-7851

    eISSN: 1521-3773

  25. Synthesis of Tetrasubstituted Furans through One-Pot Formal [3 + 2] Cycloaddition Utilizing [1,2]-Phospha-Brook Rearrangement Peer-reviewed

    Azusa Kondoh, Kohei Aita, Sho Ishikawa, Masahiro Terada

    Organic Letters 22 (5) 2105-2110 2020/03/06

    Publisher: American Chemical Society ({ACS})

    DOI: 10.1021/acs.orglett.0c00619  

    ISSN: 1523-7060

    eISSN: 1523-7052

  26. Development of Chiral Ureates as Chiral Strong Brønsted Base Catalysts Peer-reviewed

    Azusa Kondoh, Sho Ishikawa, Masahiro Terada

    Journal of the American Chemical Society 142 (8) 3724-3728 2020/02/26

    Publisher: American Chemical Society ({ACS})

    DOI: 10.1021/jacs.9b13922  

    ISSN: 0002-7863

    eISSN: 1520-5126

  27. Synthesis of diarylalkanes through an intramolecular/intermolecular addition sequence by auto-tandem catalysis with strong Brønsted base Peer-reviewed

    Azusa Kondoh, Chaoyan Ma, Masahiro Terada

    Chemical Communications 56 (74) 10894-10897 2020

    Publisher: Royal Society of Chemistry ({RSC})

    DOI: 10.1039/D0CC04512H  

    ISSN: 1359-7345

    eISSN: 1364-548X

  28. Enantioselective hydrophosphinylation of 1-alkenylphosphine oxides catalyzed by chiral strong Brønsted base Peer-reviewed

    Azusa Kondoh, Sho Ishikawa, Masahiro Terada

    Organic & Biomolecular Chemistry 18 (39) 7814-7817 2020

    Publisher: Royal Society of Chemistry ({RSC})

    DOI: 10.1039/D0OB01778G  

    ISSN: 1477-0520

  29. Synthesis of Trisubstituted Allenamides Utilizing 1,2-Rearrangement of Dialkoxyphosphoryl Moiety under Bronsted Base Catalysis Peer-reviewed

    Azusa Kondoh, Ryosuke Ozawa, Masahiro Terada

    Azusa Kondoh, Ryosuke Ozawa, Masahiro Terada 48 (9) 1164-1167 2019/09

    DOI: 10.1246/cl.190489  

    ISSN: 0366-7022

    eISSN: 1348-0715

  30. Organocatalytic Nucleophilic Substitution Reaction of gem-Difluoroalkenes with Ketene Silyl Acetals Peer-reviewed

    Azusa Kondoh, Kazumi Koda, Masahiro Terada

    Organic Letters 21 (7) 2277-2280 2019/04

    Publisher: American Chemical Society ({ACS})

    DOI: 10.1021/acs.orglett.9b00566  

    ISSN: 1523-7060

    eISSN: 1523-7052

  31. Enantioselective Intramolecular Nicholas Reaction Catalyzed by Chiral Phosphoric Acid: Enantioconvergent Synthesis of Seven‐Membered Cyclic Ethers from Racemic Diols Peer-reviewed

    Yusuke Ota, Azusa Kondoh, Masahiro Terada

    Angewandte Chemie 130 (42) 14113-14117 2018/10/15

    Publisher: Wiley

    DOI: 10.1002/ange.201808239  

  32. Cover Feature: Efficient Synthesis of Polysubstituted Pyrroles Based on [3+2] Cycloaddition Strategy Utilizing [1,2]-Phospha-Brook Rearrangement under Brønsted Base Catalysis (Chem. Eur. J. 57/2018) Peer-reviewed

    Azusa Kondoh, Akio Iino, Sho Ishikawa, Takuma Aoki, Masahiro Terada

    Chemistry - A European Journal 24 (57) 15246-15253 2018/10

    Publisher: Wiley

    DOI: 10.1002/chem.201804743  

    ISSN: 0947-6539

    eISSN: 1521-3765

  33. Efficient Synthesis of Polysubstituted Pyrroles Based on [3+2] Cycloaddition Strategy Utilizing [1,2]-Phospha-Brook Rearrangement under Brønsted Base Catalysis Peer-reviewed

    Azusa Kondoh, Akio Iino, Sho Ishikawa, Takuma Aoki, Masahiro Terada

    Chemistry - A European Journal 24 (57) 15246-15253 2018/10

    Publisher: Wiley

    DOI: 10.1002/chem.201803809  

    ISSN: 0947-6539

    eISSN: 1521-3765

  34. Organocatalytic Arylation of α-Ketoesters Based on Umpolung Strategy: Phosphazene-Catalyzed SN Ar Reaction Utilizing [1,2]-Phospha-Brook Rearrangement Peer-reviewed

    Azusa Kondoh, Takuma Aoki, Masahiro Terada

    Chemistry - A European Journal 24 (50) 13110-13113 2018/09

    Publisher: Wiley

    DOI: 10.1002/chem.201803218  

    ISSN: 0947-6539

    eISSN: 1521-3765

  35. Brønsted Base-Catalyzed Reductive Cyclization of Alkynyl α-Iminoesters through Auto-Tandem Catalysis Peer-reviewed

    Azusa Kondoh, Masahiro Terada

    Organic Letters 20 (17) 5309-5313 2018/09

    Publisher: American Chemical Society ({ACS})

    DOI: 10.1021/acs.orglett.8b02236  

    ISSN: 1523-7060

    eISSN: 1523-7052

  36. Enantioselective Intramolecular Nicholas Reaction Catalyzed by Chiral Phosphoric Acid: Enantioconvergent Synthesis of Seven-Membered Cyclic Ethers from Racemic Diols Peer-reviewed

    Yusuke Ota, Azusa Kondoh, Masahiro Terada

    Angewandte Chemie International Edition 57 (42) 13917-13921 2018/09

    Publisher: Wiley

    DOI: 10.1002/anie.201808239  

    ISSN: 1433-7851

    eISSN: 1521-3773

  37. Enantioselective Formal [3+2] Cycloaddition of Epoxides with Imines under Brønsted Base Catalysis: Synthesis of 1,3-Oxazolidines with Quaternary Stereogenic Center Peer-reviewed

    Azusa Kondoh, Shiori Akahira, Masafumi Oishi, Masahiro Terada

    Angewandte Chemie - International Edition 57 (21) 6299-6303 2018/05/22

    Publisher: Wiley-VCH Verlag

    DOI: 10.1002/anie.201802468  

    ISSN: 1521-3773 1433-7851

    eISSN: 1521-3773

  38. Enantioselective Formal [3+2] Cycloaddition of Epoxides with Imines under Brønsted Base Catalysis: Synthesis of 1,3‐Oxazolidines with Quaternary Stereogenic Center Peer-reviewed

    Azusa Kondoh, Shiori Akahira, Masafumi Oishi, Masahiro Terada

    Angewandte Chemie 130 (21) 6407-6411 2018/05/22

    Publisher: Wiley

    DOI: 10.1002/ange.201802468  

  39. Brønsted Base-Catalyzed Umpolung Intramolecular Cyclization of Alkynyl Imines Peer-reviewed

    Azusa Kondoh, Masahiro Terada

    Chemistry - A European Journal 24 (16) 3998-4001 2018/03/15

    Publisher: Wiley-VCH Verlag

    DOI: 10.1002/chem.201800219  

    ISSN: 1521-3765 0947-6539

    eISSN: 1521-3765

  40. Enantioselective direct Mannich-type reactions of 2-benzylpyridine N-oxides catalyzed by chiral bis(guanidino)iminophosphorane organosuperbase Peer-reviewed

    Qiupeng Hu, Azusa Kondoh, Masahiro Terada

    Chemical Science 9 (18) 4348-4351 2018

    Publisher: Royal Society of Chemistry

    DOI: 10.1039/c8sc00808f  

    ISSN: 2041-6539 2041-6520

    eISSN: 2041-6539

  41. Chiral Brønsted acid-catalyzed intramolecular SN2′ reaction for enantioselective construction of a quaternary stereogenic center Peer-reviewed

    Masahiro Shimizu, Jun Kikuchi, Azusa Kondoh, Masahiro Terada

    Chemical Science 9 (26) 5747-5757 2018

    Publisher: Royal Society of Chemistry ({RSC})

    DOI: 10.1039/C8SC01942H  

    ISSN: 2041-6520

    eISSN: 2041-6539

  42. Intramolecular addition of benzyl anion to alkyne utilizing [1,2]-phospha-Brook rearrangement under Bronsted base catalysis Peer-reviewed

    Azusa Kondoh, Ryosuke Ozawa, Takuma Aoki, Masahiro Terada

    ORGANIC & BIOMOLECULAR CHEMISTRY 15 (35) 7277-7281 2017/09

    DOI: 10.1039/c7ob02059g  

    ISSN: 1477-0520

    eISSN: 1477-0539

  43. Synthesis of Indolizine Derivatives Utilizing [1,2]-Phospha-Brook Rearrangement/Cycloisomerization Sequence Peer-reviewed

    Azusa Kondoh, Kazumi Koda, Yuji Kamata, Masahiro Terada

    CHEMISTRY LETTERS 46 (7) 1020-1023 2017/07

    DOI: 10.1246/cl.170377  

    ISSN: 0366-7022

    eISSN: 1348-0715

  44. Synthesis of Enantioenriched gamma-Amino-alpha,beta-unsaturated Esters Utilizing Palladium-Catalyzed Rearrangement of Allylic Carbamates for Direct Application to Formal [3+2] Cycloaddition Peer-reviewed

    Azusa Kondoh, Yuji Kamata, Masahiro Terada

    ORGANIC LETTERS 19 (7) 1682-1685 2017/04

    DOI: 10.1021/acs.orglett.7b00471  

    ISSN: 1523-7060

    eISSN: 1523-7052

  45. Generation and Application of Homoenolate Equivalents Utilizing [1,2]- Phospha-Brook Rearrangement under Bronsted Base Catalysis Peer-reviewed

    Azusa Kondoh, Takuma Aoki, Masahiro Terada

    CHEMISTRY-A EUROPEAN JOURNAL 23 (12) 2769-2773 2017/02

    DOI: 10.1002/chem.201605673  

    ISSN: 0947-6539

    eISSN: 1521-3765

  46. Enantioconvergent Nucleophilic Substitution Reaction of Racemic Alkyne-Dicobalt Complex (Nicholas Reaction) Catalyzed by Chiral Bronsted Acid Peer-reviewed

    Masahiro Terada, Yusuke Ota, Feng Li, Yasunori Toda, Azusa Kondoh

    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 138 (34) 11038-11043 2016/08

    DOI: 10.1021/jacs.6b05948  

    ISSN: 0002-7863

  47. Novel Methodology for the Efficient Synthesis of 3-Aryloxindoles: [1,2]-Phospha-Brook Rearrangement-Palladium-Catalyzed Cross-Coupling Sequence Peer-reviewed

    Azusa Kondoh, Akira Takei, Masahiro Terada

    SYNLETT 27 (12) 1848-1853 2016/07

    DOI: 10.1055/s-0035-1561859  

    ISSN: 0936-5214

    eISSN: 1437-2096

  48. Construction of Vicinal Quaternary Stereogenic Centers by Enantioselective Direct Mannich-Type Reaction Using a Chiral Bis(guanidino)iminophosphorane Catalyst Peer-reviewed

    Tadahiro Takeda, Azusa Kondoh, Masahiro Terada

    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 55 (15) 4734-4737 2016/04

    DOI: 10.1002/anie.201601352  

    ISSN: 1433-7851

    eISSN: 1521-3773

  49. Chiral Bronsted acid-catalyzed enantioselective Friedel-Crafts reaction of 2-methoxyfuran with aliphatic ketimines generated in situ Peer-reviewed

    Azusa Kondoh, Yusuke Ota, Takazumi Komuro, Fuyuki Egawa, Kyohei Kanomata, Masahiro Terada

    CHEMICAL SCIENCE 7 (2) 1057-1062 2016

    DOI: 10.1039/c5sc03175c  

    ISSN: 2041-6520

    eISSN: 2041-6539

  50. Bronsted base-catalyzed three-component coupling reaction of alpha-ketoesters, imines, and diethyl phosphite utilizing [1,2]-phospha-Brook rearrangement Peer-reviewed

    Azusa Kondoh, Masahiro Terada

    ORGANIC & BIOMOLECULAR CHEMISTRY 14 (20) 4704-4711 2016

    DOI: 10.1039/c6ob00739b  

    ISSN: 1477-0520

    eISSN: 1477-0539

  51. Enantioselective intramolecular cyclization of alkynyl esters catalyzed by a chiral Bronsted base Peer-reviewed

    Azusa Kondoh, Hoa Thi Quynh Tran, Kyoko Kimura, Masahiro Terada

    CHEMICAL COMMUNICATIONS 52 (33) 5726-5729 2016

    DOI: 10.1039/c6cc01690a  

    ISSN: 1359-7345

    eISSN: 1364-548X

  52. Synthesis of 2,3-allenylamides utilizing [1,2]-phospha-Brook rearrangement and their application to gold-catalyzed cycloisomerization providing 2-aminofuran derivatives Peer-reviewed

    Azusa Kondoh, Sho Ishikawa, Takuma Aoki, Masahiro Terada

    CHEMICAL COMMUNICATIONS 52 (84) 12513-12516 2016

    DOI: 10.1039/c6cc06591k  

    ISSN: 1359-7345

    eISSN: 1364-548X

  53. Enantioselective Addition of a 2-Alkoxycarbonyl-1,3-dithiane to Imines Catalyzed by a Bis(guanidino)iminophosphorane Organosuperbase Peer-reviewed

    Azusa Kondoh, Masafumi Oishi, Tadahiro Takeda, Masahiro Terada

    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 54 (52) 15836-15839 2015/12

    DOI: 10.1002/anie.201508178  

    ISSN: 1433-7851

    eISSN: 1521-3773

  54. Synthesis of Phenanthrene Derivatives by Intramolecular Cyclization Utilizing the [1,2]-Phospha-Brook Rearrangement Catalyzed by a Bronsted Base Peer-reviewed

    Azusa Kondoh, Takuma Aoki, Masahiro Terada

    CHEMISTRY-A EUROPEAN JOURNAL 21 (36) 12577-12580 2015/09

    DOI: 10.1002/chem.201501377  

    ISSN: 0947-6539

    eISSN: 1521-3765

  55. Ring Expansion of Epoxides under Bronsted Base Catalysis: Formal [3+2] Cycloaddition of beta,gamma-Epoxy Esters with Imines Providing 2,4,5-Trisubstituted 1,3-Oxazolidines Peer-reviewed

    Azusa Kondoh, Kenta Odaira, Masahiro Terada

    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 54 (38) 11240-11244 2015/09

    DOI: 10.1002/anie.201505893  

    ISSN: 1433-7851

    eISSN: 1521-3773

  56. Kinetic Resolution of Racemic Amino Alcohols through Intermolecular Acetalization Catalyzed by a Chiral Bronsted Acid Peer-reviewed

    Takuto Yamanaka, Azusa Kondoh, Masahiro Terada

    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 137 (3) 1048-1051 2015/01

    DOI: 10.1021/ja512238n  

    ISSN: 0002-7863

    eISSN: 1520-5126

  57. Cover Picture: Enantioselective Addition of a 2-Alkoxycarbonyl-1,3-dithiane to Imines Catalyzed by a Bis(guanidino)iminophosphorane Organosuperbase (Angew. Chem. Int. Ed. 52/2015) Peer-reviewed

    Azusa Kondoh, Masafumi Oishi, Tadahiro Takeda, Masahiro Terada

    Angewandte Chemie International Edition 54 (52) 15587-15587 2015

    Publisher: Wiley-Blackwell

    DOI: 10.1002/anie.201510887  

  58. SYNTHESIS OF INTERMEDIARY P3 PHOSPHAZENIUM FRAMEWORK AND ITS DERIVATIZATION TO CHIRAL CATIONIC MACROCYCLES INCLUDING TWO P3 PHOSPHAZENIUM UNITS WITH HYDROGEN BOND DONOR SITES Peer-reviewed

    Masahiro Terada, Kengo Goto, Takashi Ikehara, Azusa Kondoh

    HETEROCYCLES 90 (2) 1396-1404 2015/01

    DOI: 10.3987/COM-14-S(K)98  

    ISSN: 0385-5414

    eISSN: 1881-0942

  59. Bronsted base-catalyzed alpha-oxygenation of carbonyl compounds utilizing the [1,2]-phospha-Brook rearrangement Peer-reviewed

    Azusa Kondoh, Masahiro Terada

    Organic Chemistry Frontiers 2 (7) 801-805 2015

    DOI: 10.1039/c5qo00108k  

    ISSN: 2052-4129

  60. Intramolecular Cyclization of Alkynyl alpha-Ketoanilide Utilizing [1,2]-Phospha-Brook Rearrangement Catalyzed by Phosphazene Base Peer-reviewed

    Azusa Kondoh, Takuma Aoki, Masahiro Terada

    ORGANIC LETTERS 16 (13) 3528-3531 2014/07

    DOI: 10.1021/ol501479t  

    ISSN: 1523-7060

    eISSN: 1523-7052

  61. COD ID: 4109276 Peer-reviewed

    Kondoh Azusa, Yorimitsu Hideki, Oshima Koichiro

    Crystallography Open Database 2014

  62. COD ID: 1505349 Peer-reviewed

    Kondoh Azusa, Yorimitsu Hideki, Oshima Koichiro

    Crystallography Open Database 2014

  63. Design and Synthesis of Helically Chiral Spirocyclic P3 Phosphazenes and Characterization of Their Onium Salts Peer-reviewed

    Masahiro Terada, Kengo Goto, Masafumi Oishi, Tadahiro Takeda, Eunsang Kwon, Azusa Kondoh

    SYNLETT 24 (19) 2531-2534 2013/12

    DOI: 10.1055/s-0033-1340058  

    ISSN: 0936-5214

    eISSN: 1437-2096

  64. Brønsted base catalyzed [2,3]-Wittig/phospha-Brook tandem rearrangement sequence Peer-reviewed

    Azusa Kondoh, Masahiro Terada

    Organic Letters 15 (17) 4568-4571 2013/09/06

    Publisher: American Chemical Society ({ACS})

    DOI: 10.1021/ol402144q  

    ISSN: 1523-7060 1523-7052

    eISSN: 1523-7052

  65. Increasing the Structural Span of Alkyne Metathesis Peer-reviewed

    Peter Persich, Josep Llaveria, Rudy Lhermet, Teresa de Haro, Robert Stade, Azusa Kondoh, Alois Fürstner

    Chemistry - A European Journal 19 (39) 13047-13058 2013/09/03

    Publisher: Wiley-Blackwell

    DOI: 10.1002/chem.201302320  

  66. Total Synthesis of Nominal Gobienine A Peer-reviewed

    Azusa Kondoh, Alexander Arlt, Barbara Gabor, Alois Fürstner

    Chemistry - A European Journal 19 (24) 7731-7738 2013/04

    Publisher: Wiley-Blackwell

    DOI: 10.1002/chem.201300827  

  67. Phosphazene-catalyzed intramolecular cyclization of nitrogen-tethered alkynyl esters Peer-reviewed

    Azusa Kondoh, Kenichi Ando, Masahiro Terada

    CHEMICAL COMMUNICATIONS 49 (87) 10254-10256 2013

    DOI: 10.1039/c3cc46100a  

    ISSN: 1359-7345

    eISSN: 1364-548X

  68. Optimized Synthesis, Structural Investigations, Ligand Tuning and Synthetic Evaluation of Silyloxy-Based Alkyne Metathesis Catalysts Peer-reviewed

    Johannes Heppekausen, Robert Stade, Azusa Kondoh, Guenter Seidel, Richard Goddard, Alois Fuerstner

    CHEMISTRY-A EUROPEAN JOURNAL 18 (33) 10281-10299 2012/08

    DOI: 10.1002/chem.201200621  

    ISSN: 0947-6539

    eISSN: 1521-3765

  69. CCDC 805498: Experimental Crystal Structure Determination Peer-reviewed

    Iwasaki M, Fujino D, Wada T, Kondoh A, Yorimitsu H, Oshima K

    Cambridge Structural Database 2012

    DOI: 10.5517/ccw15tw  

  70. Palladium-Catalyzed Alkynylthiolation of Alkynes with Triisopropylsilylethynyl Sulfide Peer-reviewed

    Masayuki Iwasaki, Daishi Fujino, Tatsuya Wada, Azusa Kondoh, Hideki Yorimitsu, Koichiro Oshima

    CHEMISTRY-AN ASIAN JOURNAL 6 (12) 3190-3194 2011/12

    DOI: 10.1002/asia.201100643  

    ISSN: 1861-4728

  71. Catalysis-Based and Protecting-Group-Free Totall Syntheses of the Marine Oxylipins Hybridalactone and the Ecklonialactones A, B, and C Peer-reviewed

    Volker Hickmann, Azusa Kondoh, Barbara Gabor, Manuel Alcarazo, Alois Fuerstner

    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 133 (34) 13471-13480 2011/08

    DOI: 10.1021/ja204027a  

    ISSN: 0002-7863

  72. CCDC 753397: Experimental Crystal Structure Determination Peer-reviewed

    Kondoh A, Yorimitsu H, Oshima K

    Cambridge Structural Database 2011

    DOI: 10.5517/cct8z45  

  73. Synthesis of 2-Indolylphosphines by Palladium-Catalyzed Annulation of 1-Alkynylphosphine Sulfides with 2-Iodoanilines Peer-reviewed

    Azusa Kondoh, Hideki Yorimitsu, Koichiro Oshima

    ORGANIC LETTERS 12 (7) 1476-1479 2010/04

    DOI: 10.1021/ol1001544  

    ISSN: 1523-7060

  74. Palladium-Catalyzed Addition of Silyl-Substituted Chloroalkynes to Terminal Alkynes Peer-reviewed

    Tatsuya Wada, Masayuki Iwasaki, Azusa Kondoh, Hideki Yorimitsu, Koichiro Oshima

    CHEMISTRY-A EUROPEAN JOURNAL 16 (35) 10671-10674 2010

    DOI: 10.1002/chem.201000865  

    ISSN: 0947-6539

  75. 1-Alkynylphosphines and Their Derivatives as Key Starting Materials in Creating New Phosphines Peer-reviewed

    Azusa Kondoh, Hideki Yorimitsu, Koichiro Oshima

    CHEMISTRY-AN ASIAN JOURNAL 5 (3) 398-409 2010

    DOI: 10.1002/asia.200900447  

    ISSN: 1861-4728

  76. Rhodium-catalyzed dehydrogenative borylation of cyclic alkenes Peer-reviewed

    Azusa Kondoh, Timothy F. Jamison

    CHEMICAL COMMUNICATIONS 46 (6) 907-909 2010

    DOI: 10.1039/b921387b  

    ISSN: 1359-7345

  77. Radical Addition of Polyhaloalkanes to 2-Ethynyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Peer-reviewed

    Tatsuya Wada, Yuto Sumida, Azusa Kondoh, Hideki Yorimitsu, Koichiro Oshima

    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN 82 (11) 1433-1435 2009/11

    DOI: 10.1246/bcsj.82.1433  

    ISSN: 0009-2673

    eISSN: 1348-0634

  78. Nickel-catalyzed cross-coupling reactions of alkyl aryl sulfides and alkenyl alkyl sulfides with alkyl Grignard reagents using (Z)-3,3-dimethyl-1,2-bis(diphenylphosphino)but-1-ene as ligand Peer-reviewed

    Shigenari Kanemura, Azusa Kondoh, Hideki Yorimitsu, Koichiro Oshima

    SYNTHESIS-STUTTGART 2008 (16) 2659-2664 2008/08

    DOI: 10.1055/s-2008-1067193  

    ISSN: 0039-7881

  79. Regio- and stereoselective hydroamidation of 1-alkynylphosphine sulfides catalyzed by cesium base Peer-reviewed

    Azusa Kondoh, Hideki Yorimitsu, Koichiro Oshima

    ORGANIC LETTERS 10 (14) 3093-3095 2008/07

    DOI: 10.1021/ol8010979  

    ISSN: 1523-7060

    eISSN: 1523-7052

  80. Regio- and stereoselective additions of diphenyldithiophosphinic acid to N-(1-alkynyl)amides and 1-alkynyl sulfides Peer-reviewed

    Shigenari Kanemura, Azusa Kondoh, Hiroto Yasui, Hideki Yorimitsu, Koichiro Oshima

    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN 81 (4) 506-514 2008/04

    DOI: 10.1246/bcsj.81.506  

    ISSN: 0009-2673

    eISSN: 1348-0634

  81. Rhodium-catalyzed reaction of 1-alkynylphosphines with water yielding (E)-1-alkenylphosphine oxides Peer-reviewed

    Azusa Kondoh, Hideki Yorimitsu, Koichiro Oshima

    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN 81 (4) 502-505 2008/04

    DOI: 10.1246/bcsj.81.502  

    ISSN: 0009-2673

    eISSN: 1348-0634

  82. Intermolecular radical addition of alkylthio- and arylthiodiphenylphosphines to terminal alkynes Peer-reviewed

    Tatsuya Wada, Azusa Kondoh, Hideki Yorimitsu, Koichiro Oshima

    ORGANIC LETTERS 10 (6) 1155-1157 2008/03

    DOI: 10.1021/ol800059n  

    ISSN: 1523-7060

  83. Synthesis of bulky arylphosphanes by rhodium-catalyzed formal [2+2+2] cycloaddition reaction and their use as ligands Peer-reviewed

    Takayuki Kobatake, Azusa Kondoh, Suguru Yoshida, Hideki Yorimitsu, Koichiro Oshima

    CHEMISTRY-AN ASIAN JOURNAL 3 (8-9) 1613-1619 2008

    DOI: 10.1002/asia.200800102  

    ISSN: 1861-4728

  84. Synthesis of bulky phosphines by rhodium-catalyzed formal [2+2+2] cycloaddition reactions of tethered diynes with 1-alkynylphosphine sulfides Peer-reviewed

    Azusa Kondoh, Hideki Yorimitsu, Koichiro Oshima

    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 129 (22) 6996-+ 2007/06

    DOI: 10.1021/ja071622o  

    ISSN: 0002-7863

  85. Carbocupration of 1-alkynylphosphines followed by trapping with electrophiles Peer-reviewed

    Shigenari Kanemura, Azusa Kondoh, Hideki Yorimitsu, Koichiro Oshima

    ORGANIC LETTERS 9 (10) 2031-2033 2007/05

    DOI: 10.1021/ol0706657  

    ISSN: 1523-7060

  86. Copper-catalyzed anti-hydrophosphination reaction of 1-alkynylphosphines with diphenylphosphine providing (Z)-1,2-diphosphino-1-alkenes Peer-reviewed

    Azusa Kondoh, Hideki Yorimitsu, Koichiro Oshima

    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 129 (13) 4099-4104 2007/04

    DOI: 10.1021/ja070048d  

    ISSN: 0002-7863

  87. Palladium-catalyzed anti-hydrothiolation of 1-alkynylphosphines Peer-reviewed

    Azusa Kondoh, Hideki Yorimitsu, Koichiro Oshima

    ORGANIC LETTERS 9 (7) 1383-1385 2007/03

    DOI: 10.1021/ol0702876  

    ISSN: 1523-7060

  88. CCDC 601317: Experimental Crystal Structure Determination Peer-reviewed

    Kondoh A, Yorimitsu H, Oshima K

    Cambridge Structural Database 2007

    DOI: 10.5517/ccn5qbv  

  89. A new approach to 4-aryl-1,3-butanediols by cobalt-catalyzed sequential radical cyclization-arylation reaction of silicon-tethered 6-iodo-1-hexene derivatives Peer-reviewed

    Hidenori Someya, Azusa Kondoh, Akinori Sato, Hirohisa Ohmiya, Hideki Yorimitsu, Koichiro Oshima

    SYNLETT 2006 (18) 3061-3064 2006/11

    DOI: 10.1055/s-2006-951508  

    ISSN: 0936-5214

  90. Nucleophilic aromatic substitution reaction of nitroarenes with alkyl- or arylthio groups in dimethyl sulfoxide by means of cesium carbonate Peer-reviewed

    A Kondoh, H Yorimitsu, K Oshima

    TETRAHEDRON 62 (10) 2357-2360 2006/03

    DOI: 10.1016/j.tet.2005.11.073  

    ISSN: 0040-4020

  91. Stereoselective hydrothiolation of alkynes catalyzed by cesium base: Facile access to (Z)-1-alkenyl sulfides Peer-reviewed

    A Kondoh, K Takami, H Yorimitsu, K Oshima

    JOURNAL OF ORGANIC CHEMISTRY 70 (16) 6468-6473 2005/08

    DOI: 10.1021/jo050931z  

    ISSN: 0022-3263

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Misc. 9

  1. Chiral Organosuperbase Catalysts as Useful Tools for Developing Enantioselective Reactions

    Azusa Kondoh, Masahiro Terada

    ALDRICHIMICA ACTA 55 (1) 9-15 2022

    ISSN: 0002-5100

  2. Development of molecular transformations on the basis of catalytic generation of anionic species by organosuperbase

    Azusa Kondoh, Masahiro Terada

    Bulletin of the Chemical Society of Japan 94 (1) 339-356 2021

    DOI: 10.1246/BCSJ.20200308  

    ISSN: 0009-2673

    eISSN: 1348-0634

  3. 基質認識型有機酸・塩基触媒の設計開発

    近藤 梓, 菊池 隼, 寺田 眞浩

    触媒年鑑 触媒技術の動向と展望 2019 24 2019/04

  4. 有機分子触媒 有機超強塩基触媒が拓く新たな炭素‐炭素結合生成反応

    近藤梓, 寺田眞浩

    Chemical Times 2018 (2) 8‐13 2018/04

    ISSN: 0285-2446

  5. Novel Transformations Utilizing [1,2]-Phospha-Brook Rearrangement Under Bronsted Base Catalysis

    近藤梓, 寺田眞浩

    有機合成化学協会誌 76 (2) 151‐163-163 2018/02/01

    DOI: 10.5059/yukigoseikyokaishi.76.151  

    ISSN: 0037-9980

  6. 強塩基性触媒による新たな炭素‐炭素結合形成 脱プロトン化で何ができるか

    近藤梓

    化学と工業 70 (7) 625‐626 2017/07/01

    ISSN: 0022-7684

  7. 有機分子触媒がもたらす新しい有機合成の形 不斉有機超強塩基触媒が拓く新たなエナンチオ選択的付加反応

    近藤梓, 寺田眞浩

    月刊ファインケミカル 46 (3) 29‐34-34 2017/03/15

    Publisher: シーエムシー出版

    ISSN: 0913-6150

  8. 触媒の”ハイブリッド” 金属触媒と有機触媒の組合せによる触媒反応

    近藤梓, 寺田眞浩

    化学 67 (6) 66-67 2012/06/01

    ISSN: 0451-1964

  9. Palladium-Catalyzed 1,1-Difunctionalization of Terminal Alkenes

    Azusa Kondoh

    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN 69 (10) 1160-1161 2011/10

    DOI: 10.5059/yukigoseikyokaishi.69.1160  

    ISSN: 0037-9980

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Books and Other Publications 5

  1. Enantioselective Organocatalysis: Catalysts, Reactions, and Applications

    Peter I. Dalko

    2025/11

    ISBN: 9783527353408

  2. The chemistry of organocobalt compounds

    Gosmini, Corinne, Marek, Ilan

    Wiley 2023/11/14

    ISBN: 1119692016

  3. Asymmetric Organocatalysis: New Strategies, Catalysts, and Opportunities, 2 Volumes

    Albrecht, Lukasz, Albrecht, Anna, Dell'Amico, Luca

    Wiley-VCH 2022/12

    ISBN: 9783527349074

  4. Catalytic asymmetric synthesis

    Akiyama, Takahiko, Ojima, Iwao

    John Wiley & Sons 2022/05

    ISBN: 9781119736394

  5. Atropisomerism and axial chirality

    Lassaletta, José M.

    World Scientific 2019/06

    ISBN: 9781786346452

Research Projects 8

  1. Development of advanced molecular transformations based on innovative molecular design of higher order organosuperbase catalysts enabling molecular recognition

    Offer Organization: Japan Society for the Promotion of Science

    System: Grants-in-Aid for Scientific Research

    Category: Grant-in-Aid for Scientific Research (S)

    Institution: Tohoku University

    2022/04/27 - 2027/03/31

  2. 基質設計と反応開発を基軸とした縮環式複素芳香族化合物の置換位置選択的合成法の確立

    近藤 梓

    Offer Organization: 日本学術振興会

    System: 科学研究費助成事業

    Category: 基盤研究(C)

    Institution: 東北大学

    2023/04/01 - 2026/03/31

    More details Close

    高度に官能基化された多置換の縮環式複素芳香族化合物の置換位置選択的合成法を確立することを目的として、独自に開拓した複素芳香環構築の方法論に基づいて新たな芳香環構築法の開発に取り組んだ。具体的には、フラン環とチオフェン環が縮環したチエノ[3,2-b]フランの合成法の開発に取り組んだ。まず、これまでに独自に確立した三置換3-ヨードフラン合成法を応用することで、2-アルキニル-3-ベンジルチオフランの合成法を確立した。さらにこの化合物を基質とし、ブレンステッド塩基を用いた分子内環化反応を開発することで、一般性の高い合成法がほとんど確立されていない四置換チエノ[3,2-b]フランの合成法を開発することに成功した。この合成法を用いれば、多様な置換基が望みの位置に導入されたチエノ[3,2-b]フランを簡便に合成することが可能である。また、この合成法を応用することで、さらに合成例が少ないフラン環とセレノフェン環が縮環下セレノ[3,2-b]フランを合成できることも明らかにした。これらの成果は、物質供給を通して有機機能材料の開発研究への応用展開が期待される成果である。現在論文投稿に向けた準備を行っているところである。 一方、縮環式複素芳香族化合物の合成法としてこれまでに開発した分子内アンチカルボメタル化の拡充に取り組む中で、新たな骨格転位反応を見いだした。今後検討を進めることで、反応機構的にも新しい、画期的な骨格構築法の確立が期待される。

  3. Development of advanced molecular transformations based on innovative molecular design of higher order organosuperbase catalysts enabling molecular recognition

    Offer Organization: Japan Society for the Promotion of Science

    System: Grants-in-Aid for Scientific Research

    Category: Grant-in-Aid for Scientific Research (A)

    Institution: Tohoku University

    2022/04/01 - 2025/03/31

  4. Development of Functional Organosuperbase Catalysts Enabling Molecular Recognition

    TERADA Masahiro

    Offer Organization: Japan Society for the Promotion of Science

    System: Grants-in-Aid for Scientific Research

    Category: Grant-in-Aid for Scientific Research (S)

    Institution: Tohoku University

    2016/05/31 - 2021/03/31

    More details Close

    Brønsted bases have been extensively employed for activation of reactants having an acidic proton. Among these, organobases were commonly utilized as a reagent for molecular transformations, however applicable transformations have been quite limited because of these less basic properties. In recent years, intensive interest has been devoted to the development of organosuperbases, although little attention has been devoted to the catalytic use of these fascinating molecules. We focused on the utilization of these organosuperbase as a catalyst and the development of functional organosuperbase catalysts enabling molecular recognition, namely, chiral organosuperbases. The purpose of this research is that the design and synthesis of chiral organosuperbases, which have unprecedent and remarkable catalytic activity, high selectivity, and construction of catalyst-recycling system. As the result, we have successfully developed a new type of chiral organosuperbase catalysts.

  5. Development of New Method for Synthesis of Heterocyclic Compounds Utilizing Cycloaddition Reactions Catalyzed by Bronsted Base

    Kondoh Azusa

    Offer Organization: Japan Society for the Promotion of Science

    System: Grants-in-Aid for Scientific Research

    Category: Grant-in-Aid for Scientific Research (C)

    Institution: Tohoku University

    2016/04/01 - 2019/03/31

    More details Close

    With the aim of establishing the novel synthetic methods of multi-substituted five-membered heterocyclic compounds in a highly stereoselective manner, we investigated the formal [3+2] cycloaddition reactions of three-membered ring compounds, such as epoxides, aziridines, and cyclopropanes, with unsaturated compounds on the basis of our original methodology utilizing Bronsted base catalysis. As a result, we successfully developed a novel enantioselective formal [3+2] cycloaddition reaction of β,γ-epoxysulfones with imines under Bronsted base catalysis. The chiral bis(guanidino)iminophosphorane as a chiral organosuperbase catalyst enabled the enantioselective reaction, owing to its strong basicity and high stereocontrolling ability, to provide enantioenriched 1,3-oxazolidines, which are useful building blocks in organic synthesis, in a highly diastereo- and enantioselective manner.

  6. 基質認識型・超強塩基性有機分子触媒の創製

    寺田 眞浩, 近藤 梓

    Offer Organization: 日本学術振興会

    System: 科学研究費助成事業

    Category: 基盤研究(A)

    Institution: 東北大学

    2016/04/01 - 2017/03/31

    More details Close

    ホスファゼンはその単位構造であるイミノホスホランユニット(P=N構造)の連結数が増すごとに塩基性が向上する。この化学的特質に着目するとともに、イミノホスホランに効果的な基質認識能を付与するため、その両端にグアニジンもしくはホスファゼンユニットを二つ導入したC2対称性を有する触媒分子群、ならびに水素結合ドナーとなる酸性官能基と超強塩基性官能基とを組み合わせた酸塩基二官能基型の触媒分子群を「基質認識型・超強塩基性有機分子触媒」として設計開発することを計画した。 これまでの研究で擬C2対称性を有するスピロ環不斉ビス(グアニジノ)イミノホスホランの開発に成功し、超強塩基性を示す有機分子触媒として優れた機能を示すことを明らかにした。一方、スピロ環不斉P3ホスファゼンの基本骨格の合成にも成功し、これら超強塩基性有機分子触媒の各種誘導体の合成とそれらを用いた触媒反応系の開拓を主に検討した。 スピロ不斉ビス(グアニジノ)イミノホスホランを不斉触媒とする反応開発では、超強塩基性であるがゆえに、従来の有機塩基では活性化が困難であったプロ求核剤から活性種を発生させることに成功し、特にチオノラクトンをプロ求核剤としたケチミンとのMannich反応では高いエナンチオ選択性で生成物を得ることに成功し、スピロ不斉ビス(グアニジノ)イミノホスホランの基質認識型・超強塩基性有機分子触媒としての有用性を示すことができた。

  7. Development of Novel Chiral Nucleophilic Catalyst Possessing Triazadiphosphole Structure and Its Application to Enantioselective Acylation

    Kondoh Azusa

    Offer Organization: Japan Society for the Promotion of Science

    System: Grants-in-Aid for Scientific Research

    Category: Grant-in-Aid for Young Scientists (B)

    Institution: Tohoku University

    2013/04/01 - 2016/03/31

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    With the aim of developing a novel nucleophilic catalyst possessing both of a stereogenic center and a hydrogen-bond donor cite at the position adjacent to the nucleophilic cite, a 1,2,4-triazadiphosphole catalyst was designed and investigated. As a result, we achieved the short-step construction of the triazadiphosphole framework. The catalytic activity of the triazadiphosphole thus synthesized was evaluated, and the compound was found to function as an organobase although the application as a nucleophilic catalystwas not succeeded. After the revision of catalyst structure, a novel bifunctional chiral strong organobase catalyst, which has a quaternary ammonium moiety as a hydrogen-bond donor, was designed and synthesized. The application of the catalyst to some reactions suggested that the quaternary ammonium moiety could effectively serve as a hydrogen-bond donor and involve the stereocontrol of the reactions.

  8. アルキニルおよびアルケニルホスフィンを出発物質とする新配位子群の創製とその利用

    近藤 梓

    Offer Organization: 日本学術振興会

    System: 科学研究費助成事業

    Category: 特別研究員奨励費

    Institution: 京都大学

    2007 - 2009

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    近年、嵩高いリン配位子が遷移金属触媒反応の配位子として有用であるとして注目を集めている。しかしながらその一般的な合成法は限られており、合成できるリン配位子にも制限がある。したがって新たな嵩高いホスフィンの合成法の開発は重要かつ魅力的な研究課題である。この背景のもと、1-アルキニルホスフィン誘導体を出発物質とする嵩高いヘテロアリールホスフィンの合成法の開発を目指して種々の反応の検討を行った。その結果、パラジウム触媒と塩基の存在下、レアルキニルホスフィンスルフィドにN-アルキル-2-ヨードアニリンを作用させると環化反応が進行し、2-インドリルホスフィンスルフィドが高選択的に良好な収率で得られることを見いだした。得られたホスフィンスルフィドはラジカル脱硫条件下において容易に対応する三価のホスフィンに誘導することができる。生成物はリン原子に隣接する位置に1-アルキニルホスフィンスルフィド由来の置換基を有しておりリン原子周りが非常に嵩高くなっている。 従来ヘテロアリールホスフィンはヘテロ芳香族化合物のリチオ化とそれに引き続くクロロホスフィンに対する求核置換反応によって合成されている。この方法ではリン原子の導入前にあらかじめヘテロ芳香族化合物を合成する必要があり3位に導入できる置換基にかなりの制限があった。これに対し今回見いだした方法はヘテロ芳香環の構築とリン原子の2位への選択的導入ならびに3位への置換基の導入が同時に起こるという特徴を有しており、これまでに導入が困難であった置換基の3位への導入が可能となった。 また、この方法を用いて新たに合成したホスフィンが電子豊富な塩化アリールの鈴木-宮浦カップリング反応の配位子として有用であることも明らかにした。

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