Preparation of cysteinol derivatives by highly regioselective ring opening of nonactivated chiral aziridines by thiols

被引：58

作者：

Bae, JH ^{[1
]}

Shin, SH ^{[1
]}

Park, CS ^{[1
]}

Lee, WK ^{[1
]}

机构：

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

来源：

TETRAHEDRON | 1999年 / 55卷 / 33期

关键词：

amino acids and derivatives; chiral aziridine; ring opening;

D O I：

10.1016/S0040-4020(99)00538-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Various enantiomerically pure aziridine-a-methanol derivatives Ja-l were reacted with thiophenol in methylene chloride at room temperature to obtain ring-opening products 4a-I in high yields with excellent regioselectivity. The reaction procedure is very simple and it provides highly functionalized chiral molecules potentially useful for the synthesis of many biologically important compounds. The reaction rate was found to increase with the acidity of thiols. (C) 1999 Elsevier Science Ltd. All rights reserved.

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页码：10041 / 10046

页数：6

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