Reaction of allylzinc reagents and zinc enolates of ketones with α-amidoalkylphenyl sulfones

被引：42

作者：

Petrini, M

Profeta, R

Righi, P

机构：

[1] Univ Camerino, Dipartimento Sci Chim, I-62032 Camerino, Italy

[2] Univ Bologna, Dipartimento Chim Organ A Mangini, I-40136 Bologna, Italy

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2002年 / 67卷 / 13期

关键词：

D O I：

10.1021/jo025606f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

a-Amidoalkylphenyl sulfones behave as N-acylimino equivalents in the reaction with functionalized allylzinc reagents. The addition products obtained using the zinc derivative of ethyl 2-(bromomethyl)acrylate can be readily transformed into alpha-methylene-gamma-lactams using different cyclization procedures. The allylzinc reagent obtained from 3-bromo-1-acetoxy-1-propene directly affords protected 1,2-amino alcohols with a preference for the anti stereoisomer, regardless of the structure of the alpha-amidoalkylphenyl sulfone employed. This procedure can be extended to the use of zinc enolates obtained from a-bromo ketones and leads to the synthesis of N-protected beta-amino ketones.

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页码：4530 / 4535

页数：6

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