The highly enantioselective 1,3-dipolar cycloaddition of alkyl glyoxylate-derived nitrones to E-crotonaldehyde catalyzed by hybrid diamines

被引：25
作者：
Weselinski, Lukasz [1 ]
Slyk, Edyta [1 ,2 ]
Jurczak, Janusz [1 ,2 ]
机构：
[1] Univ Warsaw, Dept Chem, PL-02093 Warsaw, Poland
[2] Polish Acad Sci, Inst Organ Chem, PL-01224 Warsaw, Poland
来源：
TETRAHEDRON LETTERS | 2011年 / 52卷 / 03期
关键词：
Amino acids; Asymmetric organocatalysis; Binaphthyl derivatives; 1,3-Dipolar cycloaddition; Nitrones; GAMMA-LACTAM; ORGANOCATALYSTS; ISOXAZOLIDINES; PYRROLIDINE; ALDEHYDES;
D O I：
10.1016/j.tetlet.2010.11.015
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
1,3-Dipolar cycloaddition of alkyl glyoxylate-derived nitrones to E-crotonaldehyde can be catalyzed by hybrid diamines, obtained from (S)-BINAM and L-alpha-amino acids. The hybrid of (S)-BINAM and L-Phe was found to be the best organocatalyst. Products were obtained in good yield and diastereoselectivity as well as high enantioselectivity (82-91% cc). Subsequent transformations into functionalized pyrrolidinones have been demonstrated. (C) 2010 Elsevier Ltd. All rights reserved.
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收藏
页码：381 / 384
页数：4
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