New synthesis and ring opening of cis-3-alkylaziridine-2-carboxylates

被引：48

作者：

Lee, KD

Suh, JM

Park, JH

Ha, HJ

Choi, HG

Park, CS

Chang, JW

Lee, WK

Dong, Y

Yun, H

机构：

[1] Sogang Univ, Dept Chem, Seoul 121742, South Korea

[2] Ajou Univ, Dept Mol Sci & Technol, Suwon 442749, South Korea

来源：

TETRAHEDRON | 2001年 / 57卷 / 39期

关键词：

aziridine-2-carboxylate; homophenylalanine; beta-amino-alpha-hydroxy acid; alpha; beta-diamino acid; alpha-amino-beta-hydroxy acid;

D O I：

10.1016/S0040-4020(01)00823-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Syntheses of cis-3-alkylaziridine-2-carboxylates including cis-3-benzyl- and cis-3-phenylaziridine-2-carboxylates were achieved from the reaction of alpha -aminonitrile and alkyldiazoacetate in the presence of a Lewis acid. Asymmetric version of this reaction with the chiral alpha -methylbenzylamine was also successful for the preparation of chiral aziridines that were used for the synthesis of various amino acids including homophenylalanine, beta -amino-alpha -hydroxy acid, alpha,beta -diamino acid, and alpha -amino-beta -hydroxy acid via regioselective aziridine ring openings. (C) 2001 Elsevier Science Ltd. All rights reserved.

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页码：8267 / 8276

页数：10

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