Catalytic enantioselective direct Michael additions of ketones to alkylidene malonates

被引:266
作者
Betancort, JM
Sakthivel, K
Thayumanavan, R
Barbas, CF
机构
[1] Skaggs Inst Chem Biol, La Jolla, CA 92037 USA
[2] Scripps Res Inst, Dept Mol Biol, La Jolla, CA 92037 USA
基金
美国国家卫生研究院;
关键词
asymmetric catalyst; asymmetric synthesis; Michael reaction;
D O I
10.1016/S0040-4039(01)00793-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Enantioselective direct Michael additions of ketones using (S)-1-(2-pyrroldinylmethyl)-pyrrolidine as a catalyst are described. Michael adducts with up to 91% e.e. were obtained by the reaction of alkylidene malonates with simple unactivated ketones under mild reaction conditions. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:4441 / 4444
页数:4
相关论文
共 24 条
[1]   A new multifunctional heterobimetallic asymmetric catalyst for Michael additions and tandem Michael-Aldol reactions [J].
Arai, T ;
Sasai, H ;
Aoe, K ;
Okamura, K ;
Date, T ;
Shibasaki, M .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (01) :104-106
[2]   ASYMMETRIC MICHAEL ADDITIONS - STEREOSELECTIVE ALKYLATIONS OF THE (R)-ENAMINE AND (S)-ENAMINE FROM CYCLOHEXANONE AND 2-(METHOXYMETHYL)PYRROLIDINE BY METHYL ALPHA-(METHOXYCARBONYL)CINNAMATES [J].
BLARER, SJ ;
SEEBACH, D .
CHEMISCHE BERICHTE-RECUEIL, 1983, 116 (06) :2250-2260
[3]   A proline-catalyzed asymmetric Robinson annulation reaction [J].
Bui, T ;
Barbas, CF .
TETRAHEDRON LETTERS, 2000, 41 (36) :6951-6954
[4]   ASYMMETRIC MICHAEL ADDITIONS VIA SAMP-HYDRAZONES RAMP-HYDRAZONES ENANTIOSELECTIVE 1,4-ADDITION OF METHYL KETONES TO KNOEVENAGEL ACCEPTORS [J].
ENDERS, D ;
DEMIR, AS ;
RENDENBACH, BEM .
CHEMISCHE BERICHTE-RECUEIL, 1987, 120 (10) :1731-1735
[5]   Catalytic asymmetric conjugate addition of nitroalkanes to cycloalkenones [J].
Hanessian, S ;
Pham, V .
ORGANIC LETTERS, 2000, 2 (19) :2975-2978
[6]  
HERRMAN M, 1979, J ORG CHEM, V44, P2238
[7]  
Jacobsen E. N., 1999, COMPREHENSIVE ASYMME, V1- 3
[8]   Catalytic enantioselective conjugate addition of 1,3-dicarbonyl compounds to nitroalkenes [J].
Ji, JG ;
Barnes, DM ;
Zhang, J ;
King, SA ;
Wittenberger, SJ ;
Morton, HE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (43) :10215-10216
[9]   Stable, storable, and reusable asymmetric catalyst: A novel La-linked-BINOL complex for the catalytic asymmetric Michael reaction [J].
Kim, YS ;
Matsunaga, S ;
Das, J ;
Sekine, A ;
Ohshima, T ;
Shibasaki, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (27) :6506-6507
[10]  
KRAPCHO AP, 1982, SYNTHESIS-STUTTGART, P805