Effect of addition of Lewis/Bronsted acids in the asymmetric aldol condensation catalyzed by trifluoroacetate salts of proline-based dipeptides

被引：6
|
作者：
Andreu, Cecilia [1 ]
del Olmo, Marcelli [2 ]
Asensio, Gregorio [1 ]
机构：
[1] Univ Valencia, Fac Farm, Dept Quim Organ, Valencia 46100, Spain
[2] Univ Valencia, Dept Bioquim & Biol Mol, Fac Ciencias Biol, E-46100 Valencia, Spain
来源：
TETRAHEDRON | 2012年 / 68卷 / 38期
关键词：
WATER-COMPATIBLE ORGANOCATALYSTS; TRANSITION-STATES; SEQUENCE SPACE; AMINO-ACID; ENAMINE; STEREOSELECTIVITY; PEPTIDES; PROLINETHIOAMIDES; AMINOCATALYSIS; INTERMEDIATE;
D O I：
10.1016/j.tet.2012.07.006
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Proline-based dipeptides catalyze aldol condensations with good yield and stereoselectivity after addition of zinc or sodium acetate to the trifluoroacetate peptide. The chirality of the N-terminal proline in the catalyst determines the absolute configuration of the aldol product, but stereoselectivity depends on the configuration of both amino acids, and is higher for the enantiomeric pair R-S, S-R. Regarding the nature of the second component, optimal results in both yield and stereoselectivity are obtained when neutral unbranched primary amino acids are used. (C) 2012 Elsevier Ltd. All rights reserved.
引用
收藏
页码：7966 / 7972
页数：7
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