Synthesis of higher alpha-chlorovinyl and alpha-bromovinyl amino acids: The amino protecting group determines the reaction course

被引：15

作者：

Berkowitz, DB

Pedersen, ML

Jahng, WJ

机构：

[1] Department of Chemistry, University of Nebraska-Lincoln, Lincoln

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 25期

关键词：

D O I：

10.1016/0040-4039(96)00832-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

N-Trifluoroacetyl alpha-vinyl amino esters are smoothly converted to the corresponding alpha-chlorovinyl or alpha-bromovinyl amino esters through the agency of phenyselenyl chloride or phenylselenyl bromide, respectively, followed by oxidation and pyrolysis. Exclusively the (E)-external halovinyl isomer and the internal halovinyl isomer am observed. The amino protecting group is a critical determinant of the reaction course (alkene addition vs. 5-exo-trig-like cyclization). Copyright (C) 1996 Elsevier Science Ltd.

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页码：4309 / 4312

页数：4

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