syn-selective and enantioselective direct cross-aldol reactions between aldehydes catalyzed by an axially chiral amino sulfonamide

被引:122
作者
Kano, Taichi [1 ]
Yamaguchi, Yukako [1 ]
Tanaka, Youhei [1 ]
Maruoka, Keiji [1 ]
机构
[1] Kyoto Univ, Dept Chem, Grad Sch Sci, Kyoto 6068502, Japan
关键词
aldol reaction; asymmetric catalysis; diastereoselectivity; enantioselectivity; synthetic methods;
D O I
10.1002/anie.200604640
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) Complementary to proline: An axially chiral amino sulfonamide (S)-1 was successfully applied as the catalyst to the direct cross-aldol reaction between two different aldehydes (see scheme; NMP = N-methylpyrrolidone). This catalyst has the advantage of giving mainly syn products, while proline shows the opposite anti selectivity. © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:1738 / 1740
页数:3
相关论文
共 53 条
[1]  
[Anonymous], 2004, MODERN ALDOL REACTIO
[2]  
[Anonymous], 2004, MODERN ALDOL REACTIO
[3]   Tris(trimethylsilyl)silyl-governed aldehyde cross-aldol cascade reaction [J].
Boxer, MB ;
Yamamoto, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (01) :48-49
[4]   Direct amino acid catalyzed asymmetric synthesis of polyketide sugars [J].
Casas, J ;
Engqvist, M ;
Ibrahem, I ;
Kaynak, B ;
Córdova, A .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (09) :1343-1345
[5]  
Casas J., 2005, ANGEW CHEM, V117, P1367
[6]   Amino acid catalyzed neogenesis of carbohydrates:: A plausible ancient transformation [J].
Córdova, A ;
Ibrahem, I ;
Casas, J ;
Sundén, H ;
Engqvist, M ;
Reyes, E .
CHEMISTRY-A EUROPEAN JOURNAL, 2005, 11 (16) :4772-4784
[7]   Direct catalytic asymmetric cross-aldol reactions in ionic liquid media [J].
Córdova, A .
TETRAHEDRON LETTERS, 2004, 45 (20) :3949-3952
[8]   Plausible origins of homochirality in the amino acid catalyzed neogenesis of carbohydrates [J].
Córdova, A ;
Engqvist, M ;
Ibrahem, I ;
Casas, J ;
Sundén, H .
CHEMICAL COMMUNICATIONS, 2005, (15) :2047-2049
[9]   Mechanistic insights into the chiral phosphoramide-catalyzed, enantioselective crossed-aldol reactions of aldehydes [J].
Denmark, SE ;
Bui, T .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (25) :10393-10399
[10]   Lewis base catalyzed enantioselective aldol addition of acetaldehyde-derived silyl enol ether to aldehydes [J].
Denmark, SE ;
Bui, T .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (24) :10190-10193