A versatile preparation of α,β-unsaturated lactones from homoallylic alcohols

被引：19

作者：

Keck, GE ^{[1
]}

Li, XY ^{[1
]}

Knutson, CE ^{[1
]}

机构：

[1] Univ Utah, Dept Chem, Salt Lake City, UT 84112 USA

来源：

ORGANIC LETTERS | 1999年 / 1卷 / 03期

关键词：

D O I：

10.1021/ol990632u

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] A new method for the synthesis of alpha,beta-unsaturated lactones from beta-acetoxy aldehydes by reaction with the lithium enolate of methyl acetate was developed. The reaction is relatively insensitive to structural changes in the aldehyde substrates. The process was extended to the synthesis of five-ring lactones from alpha-acetoxy aldehydes, Experimental evidence regarding the mechanism of this one-pot transformation was obtained. The observations are consistent with a pathway involving an initial aldol condensation with subsequent acyl migration, lactonization, and beta-elimination and not an enolate equilibration-aldol mechanism.

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页码：411 / 413

页数：3

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