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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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收藏
页码：8267 / 8276
页数：10
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