Cu-Catalyzed [3+3] Cycloaddition of Isocyanoacetates with Aziridines and Stereoselective Access to α,γ-Diamino Acids

被引：27

作者：

Kok, Germaine Pui Yann ^{[1
]}

Yang, Hui ^{[1
]}

Wong, Ming Wah ^{[1
]}

Zhao, Yu ^{[1
]}

机构：

[1] Natl Univ Singapore, Dept Chem, 3 Sci Dr 3, Singapore 117543, Singapore

来源：

ORGANIC LETTERS | 2018年 / 20卷 / 17期

关键词：

ENANTIOSELECTIVE SYNTHESIS; ASYMMETRIC HYDROGENATION; MULTICOMPONENT REACTIONS; ALPHA-ADDITION; AMINO-ACIDS; ISOCYANIDES; PYRROLES; CYCLIZATION; ESTERS; FUNCTIONALIZATION;

D O I：

10.1021/acs.orglett.8b01948

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We report herein an efficient Cu-catalyzed formal [3 + 3] cycloaddition of isocyanoacetates with readily available aziridines of different substitution patterns, which provides a practical access to valuable 1,4,5,6-tetrahydropyr-imidine derivatives. In particular, the use of enantiopure aziridines delivers disubstituted tetrahydropyrimidines bearing a 1,3-diamino unit in good yields as a single stereoisomer (>20:1 dr, > 99% ee). The heterocyclic products can also be easily converted to synthetically useful amino alcohol derivatives or alpha,gamma-diamino acids.

引用

页码：5112 / 5115

页数：4

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