Enantioselective Linchpin Catalysis by SOMO Catalysis: An Approach to the Asymmetric α-Chlorination of Aldehydes and Terminal Epoxide Formation

被引：152
|
作者：
Amatore, Muriel [1 ]
Beeson, Teresa D. [1 ]
Brown, Sean P. [1 ]
MacMillan, David W. C. [1 ]
机构：
[1] Princeton Univ, Merck Ctr Catalysis, Princeton, NJ 08544 USA
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2009年 / 48卷 / 28期
关键词：
epoxidation; enantioselectivity; asymmetric catalysis; organocatalysis; HYDROLYTIC KINETIC RESOLUTION; HALOGENATION; ORGANOCATALYSIS; ACTIVATION; COMPLEXES; OLEFINS; KETONES;
D O I：
10.1002/anie.200901855
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Time for SOme MOre: For the first time SOMO (singly occupied molecular orbital) activation has been exploited to allow a new approach to the α-chlorination of aldehydes. This transformation can be readily implemented as part of a linchpin catalysis approach to the enantioselective production of terminal epoxides. © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码：5121 / 5124
页数：4
相关论文
共 50 条
  • [1] Enantioselective organo-SOMO catalysis:: The α-vinylation of aldehydes
    Kim, Hahn
    MacMillan, David W. C.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (02) : 398 - +
  • [2] Enantioselective organo-SOMO catalysis: The α-vinylation of aldehydes
    Kim, Hahn
    MacMillan, David W. C.
    Journal of the American Chemical Society, 2008, 130 (02): : 398 - 399
  • [3] The intramolecular asymmetric allylation of aldehydes via organo-SOMO catalysis: A novel approach to ring construction
    Pham, Phong V.
    Ashton, Kate
    MacMillan, David W. C.
    CHEMICAL SCIENCE, 2011, 2 (08) : 1470 - 1473
  • [4] Dramatic temperature effect in asymmetric catalysis in the enantioselective addition of diethylzinc to aldehydes
    Zhang, HC
    Chan, KS
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (04): : 381 - 382
  • [5] Enantioselective Polyene Cyclization via Organo-SOMO Catalysis
    Rendler, Sebastian
    MacMillan, David W. C.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (14) : 5027 - +
  • [6] Enantioselctive SOMO catalysis: Cascade cycloadditions of aldehydes and simple olefins
    Jui, Nathan T.
    MacMillan, David W. C.
    Lee, Esther C. Y.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2011, 241
  • [7] Nature of Intermediates in Organo-SOMO Catalysis of α-Arylation of Aldehydes
    Um, Joann M.
    Gutierrez, Osvaldo
    Schoenebeck, Franziska
    Houk, K. N.
    MacMillan, David W. C.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (17) : 6001 - 6005
  • [8] A general approach to the enantioselective α-oxidation of aldehydes via synergistic catalysis
    Simonovich, Scott P.
    Van Humbeck, Jeffrey F.
    MacMillan, David W. C.
    CHEMICAL SCIENCE, 2012, 3 (01) : 58 - 61
  • [9] Nature of intermediates in organo-SOMO catalysis of a-arylation of aldehydes
    Um, Joann M.
    Gutierrez, Osvaldo
    Schoenebeck, Franziska
    Houk, K. N.
    MacMillan, David W. C.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2010, 239
  • [10] A remarkably simple α-oximation of aldehydes via organo-SOMO catalysis
    Gentili, Patrizia
    Pedetti, Silvia
    CHEMICAL COMMUNICATIONS, 2012, 48 (43) : 5358 - 5360
12345