Enantioselective organocatalytic conjugate addition of amines to α,β-unsaturated aldehydes:: one-pot asymmetric synthesis of β-amino acids and 1,3-diamines

被引:97
作者
Vesely, Jan [1 ]
Ibrahem, Ismail [1 ]
Rios, Ramon [1 ]
Zhao, Gui-Ling [1 ]
Xu, Yongmei [1 ]
Cordova, Armando [1 ]
机构
[1] Univ Stockholm, Arrhenius Lab, Dept Organ Chem, S-10691 Stockholm, Sweden
关键词
CROSS-MANNICH REACTION; CHIRAL AMMONIA EQUIVALENT; DIELS-ALDER REACTIONS; AZA-MICHAEL REACTION; ALPHA-AMINO; DERIVATIVES; CATALYSIS; 3-COMPONENT; CYCLIZATION; ENANTIOMER;
D O I
10.1016/j.tetlet.2007.01.093
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Organocatalytic asymmetric amine conjugate additions to alpha, beta-unsaturated aldehydes catalyzed by protected diarylprolinols are presented. The reactions proceed with high enantioselectivity and result in Cbz or Boc protected beta-amino aldehydes, gamma-amino alcohols, beta-amino acids and 1,3-diamines with typically 82-99% ee. (c) 2007 Elsevier Ltd. All rights reserved.
引用
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页码:2193 / 2198
页数:6
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