Origins of the double asymmetric induction on proline-catalyzed aldol reactions

被引:38
|
作者
Calderon, Felix [1 ]
Doyagueez, Elisa G. [1 ]
Cheong, Paul Ha-Yeon [2 ]
Fernandez-Mayoralas, Alfonso [1 ]
Houk, K. N. [2 ]
机构
[1] CSIC, Inst Quim Organ Gen, E-28006 Madrid, Spain
[2] Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
来源
JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 73卷 / 20期
关键词
D O I
10.1021/jo800934b
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Computational studies to elucidate the origin of the double asymmetric induction on proline-catalyzed aldol reaction have been performed using HF/6-31G(d) calculations. The computed transition structures explain the experimental data obtained.
引用
收藏
页码:7916 / 7920
页数:5
相关论文
共 50 条
  • [11] Quantum mechanical predictions of the stereoselectivities of proline-catalyzed asymmetric intermolecular aldol reactions
    Bahmanyar, S.
    Houk, K.N.
    Martin, Harry J.
    List, Benjamin
    1600, American Chemical Society (125):
  • [12] Advances in proline-catalyzed asymmetric reactions
    Li, JW
    Xu, LW
    Xia, CG
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2004, 24 (01) : 23 - 28
  • [13] The origin of stereoselectivity in proline-catalyzed intramolecular aldol reactions
    Bahmanyar, S
    Houk, KN
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (51) : 12911 - 12912
  • [14] Enamine versus Oxazolidinone: What Controls Stereoselectivity in Proline-Catalyzed Asymmetric Aldol Reactions?
    Sharma, Akhilesh K.
    Sunoj, Raghavan B.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (36) : 6373 - 6377
  • [15] Proline-catalyzed tandem aldol and alkylation reactions in alcoholic medium
    Zhao, CG
    Rajasekhar, D
    Liu, JY
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2005, 230 : U3075 - U3076
  • [16] Theoretical study of the proline-catalyzed asymmetric intramolecular aldol reaction.
    Houk, KN
    Bahmanyar, S
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2000, 219 : U218 - U218
  • [17] Effect of additives on the proline-catalyzed ketone-aldehyde aldol reactions
    Pihko, PM
    Laurikainen, KM
    Usano, A
    Nyberg, AI
    Kaavi, JA
    TETRAHEDRON, 2006, 62 (2-3) : 317 - 328
  • [18] Proline-catalyzed asymmetric aldol reactions of tetrahydro-4H-thiopyran-4-one with aldehydes
    Ward, DE
    Jheengut, V
    TETRAHEDRON LETTERS, 2004, 45 (45) : 8347 - 8350
  • [19] Enantioselective Total Synthesis of Biologically Active Natural Products Using Proline-catalyzed Asymmetric Aldol Reactions
    Komatsu, Yoshiyuki
    Ikishima, Hideaki
    Okuyama, Atsushi
    Nakamura, Mutsumi
    Kotsuki, Hiyoshizo
    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2009, 67 (01) : 65 - 75
  • [20] Proline-catalyzed ketone-aldehyde aldol reactions are accelerated by water
    Nyberg, AI
    Usano, A
    Pihko, PM
    SYNLETT, 2004, (11) : 1891 - 1896