Design of a C2-symmetric chiral pyrrolidine-based amino sulfonamide:: application to anti-selective direct asymmetric Mannich reactions

被引:46
作者
Kano, Taichi [1 ]
Hato, Yoshio [1 ]
Maruoka, Keiji [1 ]
机构
[1] Kyoto Univ, Dept Chem, Grad Sch Sci, Sakyo Ku, Kyoto 6068502, Japan
关键词
Mannich reaction; organocatalyst; tartaric acid; asymmetric synthesis;
D O I
10.1016/j.tetlet.2006.09.147
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The anti-selective direct asymmetric Mannich reaction was found to be efficiently catalyzed by the novel pyrrolidine-based amino sulfonamide (R,R)-2 prepared from L-tartaric acid. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码:8467 / 8469
页数:3
相关论文
共 28 条
[1]   The direct catalytic asymmetric cross-aldol reaction of aldehydes [J].
Alcaide, B ;
Almendros, P .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (08) :858-860
[2]  
Berkessel A, 2005, ASYMMETRIC ORGANOCATALYSIS: FROM BIOMIMETIC CONCEPTS TO APPLICATIONS IN ASYMMETRIC SYNTHESIS, P1, DOI 10.1002/3527604677
[3]   anti-selective SMP-catalyzed direct asymmetric Mannich-type reactions:: synthesis of functionalized amino acid derivatives [J].
Córdova, A ;
Barbas, CF .
TETRAHEDRON LETTERS, 2002, 43 (43) :7749-7752
[4]   A highly enantioselective route to either enantiomer of both α- and β-amino acid derivatives [J].
Córdova, A ;
Watanabe, S ;
Tanaka, F ;
Notz, W ;
Barbas, CF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (09) :1866-1867
[5]  
Dalko PI, 2001, ANGEW CHEM INT EDIT, V40, P3726, DOI 10.1002/1521-3773(20011015)40:20<3726::AID-ANIE3726>3.0.CO
[6]  
2-D
[7]   In the golden age of organocatalysis [J].
Dalko, PI ;
Moisan, L .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (39) :5138-5175
[8]   A general organocatalyst for direct α-functionalization of aldehydes:: Stereoselective C-C, C-N, C-F, C-BR, and C-S bond-forming reactions.: Scope and mechanistic insights [J].
Franzén, J ;
Marigo, M ;
Fielenbach, D ;
Wabnitz, TC ;
Kjaersgaard, A ;
Jorgensen, KA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (51) :18296-18304
[9]   Direct catalytic asymmetric Mannich-type reactions of N-(2-hydroxyacetyl)pyrrole as an ester-equivalent donor [J].
Harada, S ;
Handa, S ;
Matsunaga, S ;
Shibasaki, M .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (28) :4365-4368
[10]   Direct catalytic asymmetric anti-selective Mannich-type reactions [J].
Ibrahem, I ;
Córdova, A .
CHEMICAL COMMUNICATIONS, 2006, (16) :1760-1762