A straightforward synthesis of enantiopure 2-cyano azetidines from β-amino alcohols

被引：67

作者：

Agami, C

Couty, F

Evano, G

机构：

[1] Univ Paris 06, UMR 7611, Lab Synth Asymetr, F-75005 Paris, France

[2] Univ Versailles, CNRS, UPRESA 8086, SIRCOB, F-78035 Versailles, France

来源：

TETRAHEDRON-ASYMMETRY | 2002年 / 13卷 / 03期

关键词：

D O I：

10.1016/S0957-4166(02)00076-9

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Enantiopure 2-cyano azetidines were prepared in high yields from beta-amino alcohols. This synthesis was shown to be general and is based on two important steps: (i) chlorination of a N-cyanomethylated beta-amino alcohol and (ii) a 4-exo-trig ring closure through the alkylation of a lithiated alpha-amino nitrile. The former step is stereoselective when ephedrine-derived beta-amino alcohols are used. In the case of a phenylglycinol-derived beta-amino alcohol, this step also involves a rearrangement. (C) 2002 Elsevier Science Ltd. All rights reserved.

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页码：297 / 302

页数：6

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