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
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 23 条
[1]   Theory of asymmetric organocatalysis of aldol and related reactions: Rationalizations and predictions [J].
Allemann, C ;
Gordillo, R ;
Clemente, FR ;
Cheong, PHY ;
Houk, KN .
ACCOUNTS OF CHEMICAL RESEARCH, 2004, 37 (08) :558-569
[2]   Quantum mechanical predictions of the stereoselectivities of proline-catalyzed asymmetric intermolecular aldol reactions [J].
Bahmanyar, S ;
Houk, KN ;
Martin, HJ ;
List, B .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (09) :2475-2479
[3]   The origin of stereoselectivity in proline-catalyzed intramolecular aldol reactions [J].
Bahmanyar, S ;
Houk, KN .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (51) :12911-12912
[4]   Transition states of amine-catalyzed aldol reactions involving enamine intermediates: Theoretical studies of mechanism, reactivity, and stereoselectivity [J].
Bahmanyar, S ;
Houk, KN .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (45) :11273-11283
[5]  
Berkessel A, 2005, ASYMMETRIC ORGANOCATALYSIS: FROM BIOMIMETIC CONCEPTS TO APPLICATIONS IN ASYMMETRIC SYNTHESIS, P1, DOI 10.1002/3527604677
[6]   A proline-catalyzed asymmetric Robinson annulation reaction [J].
Bui, T ;
Barbas, CF .
TETRAHEDRON LETTERS, 2000, 41 (36) :6951-6954
[7]   Asymmetric aldol reaction using immobilized proline on mesoporous support [J].
Calderón, F ;
Fernández, R ;
Sánchez, F ;
Fernández-Mayoralas, A .
ADVANCED SYNTHESIS & CATALYSIS, 2005, 347 (10) :1395-1403
[8]   Synthesis of azasugars through a proline-catalyzed reaction [J].
Calderon, Felix ;
Doyaguez, Elisa G. ;
Fernandez-Mayoralas, Alfonso .
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (16) :6258-6261
[9]   Pipecolic acid-catalyzed direct asymmetric Mannich reactions [J].
Cheong, PHY ;
Zhang, HL ;
Thayumanavan, R ;
Tanaka, F ;
Houk, KN ;
Barbas, CF .
ORGANIC LETTERS, 2006, 8 (05) :811-814
[10]   Computational evidence for the enamine mechanism of intramolecular Aldol reactions catalyzed by proline [J].
Clemente, FR ;
Houk, KN .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (43) :5766-5768