Enantioselective ene reaction of cyclopentadiene and α,β-enals catalyzed by a diphenylprolinol silyl ether

被引:91
|
作者
Gotoh, Hiroaki [1 ]
Masui, Ryouhei [1 ]
Ogino, Hiroshi [1 ]
Shoji, Mitsuru [1 ]
Hayashi, Yujiro [1 ]
机构
[1] Tokyo Univ Sci, Fac Engn, Dept Ind Chem, Shinjuku Ku, Tokyo 1628601, Japan
关键词
asymmetric synthesis; cyclopentadiene; Diels-Alder reaction; ene reaction; organocatalysis;
D O I
10.1002/anie.200602925
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) The opposite result: A diphenylprolinol silyl ether promotes an intermolecular enantioselective ene reaction of α,β-enals with cyclopentadiene. This is the first example of cyclopentadiene acting as the ene component, and not the diene, with α,β-enals. © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:6853 / 6856
页数:4
相关论文
共 50 条
  • [21] Asymmetric Aldol Reaction of α,α-Disubstituted Acetaldehydes Catalyzed by Diphenylprolinol Silyl Ether for the Construction of Quaternary Stereogenic Centers
    Hayashi, Yujiro
    Shomura, Hiroki
    Xu, Qianqian
    Lear, Martin J.
    Sato, Itaru
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (20) : 4316 - 4319
  • [22] Asymmetric Michael Reaction of α-CF3 Thioester and α,β-Unsaturated Aldehyde Catalyzed by Diphenylprolinol Silyl Ether
    Hayashi, Yujiro
    Yamada, Tomoaki
    Sato, Misaki
    Watanabe, Shoya
    Kwon, Eunsang
    Iwasaki, Kotaro
    Umemiya, Shigenobu
    ORGANIC LETTERS, 2019, 21 (13) : 5183 - 5186
  • [23] Direct Enantioselective Organocatalytic Hydroxymethylation of Aldehydes Catalyzed by α,α-Diphenylprolinol Trimethylsilyl Ether
    Boeckman, Robert K., Jr.
    Miller, John R.
    ORGANIC LETTERS, 2009, 11 (20) : 4544 - 4547
  • [24] Mechanism of Diphenylprolinol Silyl Ether Catalyzed Michael Addition Revisitedbut Still Controversial
    Moberg, Christina
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (08) : 2160 - 2162
  • [25] Diphenylprolinol silyl ether as a catalyst in an enantioselective, catalytic, formal aza [3+3] cycloaddition reaction for the formation of enantioenriched piperidines
    Hayashi, Yujiro
    Gotoh, Hiroaki
    Masui, Ryouhei
    Ishikawa, Hayato
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (21) : 4012 - 4015
  • [26] Diphenylprolinol Silyl Ether Catalyzed Asymmetric Formal Carbo [3+3] Cycloaddition Reaction of Isopropylidenemalononitrile and α,β-Unsaturated Aldehyde
    Umekubo, Nariyoshi
    Han, Xiaolei
    Mori, Naoki
    Hayashi, Yujiro
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 2022 (26)
  • [27] Domino Michael/Michael Reaction for the Formation of Chiral Spirocycles Using a Diphenylprolinol Silyl Ether
    Hayashi, Yujiro
    Nagai, Kaito
    Umemiya, Shigenobu
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 2019 (04) : 678 - 681
  • [28] Asymmetric One-Pot Four-Component Coupling Reaction: Synthesis of Substituted Tetrahydropyrans Catalyzed by Diphenylprolinol Silyl Ether
    Ishikawa, Hayato
    Sawano, Satoshi
    Yasui, Yusuke
    Shibata, Yusuke
    Hayashi, Yujiro
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (16) : 3774 - 3779
  • [29] One-pot synthesis of chiral bicyclo[3.3.0]octatrienes using diphenylprolinol silyl ether-mediated ene-type reaction
    Gotoh, Hiroaki
    Ogino, Hiroshi
    Ishikawa, Hayato
    Hayashi, Yujiro
    TETRAHEDRON, 2010, 66 (26) : 4894 - 4899
  • [30] Two Reaction Mechanisms via Iminium Ion Intermediates: The Different Reactivities of Diphenylprolinol Silyl Ether and Trifluoromethyl-Substituted Diarylprolinol Silyl Ether
    Gotoh, Hiroaki
    Uchimaru, Tadafumi
    Hayashi, Yujiro
    CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (35) : 12337 - 12346