π-Face selective azaspirocyclization of ω-(methoxyphenyl)-N-methoxyalkylamides

被引：55

作者：

Wardrop, DJ ^{[1
]}

Burge, MS ^{[1
]}

Zhang, W ^{[1
]}

Ortíz, JA ^{[1
]}

机构：

[1] Univ Illinois, Dept Chem, Chicago, IL 60607 USA

来源：

TETRAHEDRON LETTERS | 2003年 / 44卷 / 12期

基金：

美国国家卫生研究院; 美国国家科学基金会;

关键词：

D O I：

10.1016/S0040-4039(03)00227-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel method for the stereoselective preparation of 1-azaspiranes is described. Treatment of alpha- and beta-substituted 3-(methoxyphenyl)-N-methoxypropionamides 1 with phenyliodine(III) bis(trifluoroacetate) initiates efficient azaspirocyclization, via a putative N-acylnitrenium ion intermediate, to provide cyclohexa-2,5 and 2,4-dienone spirolactams 8 and 11 with good pi-facial selectivity. Furthermore, a preliminary study indicates that this strategy is also amenable to the preparation of 1-azaspiro[5.5] undeca-2,5-dienones. (C) 2003 Elsevier Science Ltd. All rights reserved.

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页码：2587 / 2591

页数：5

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