SYNTHESIS OF ALPHA-METHYLENE BETA-LACTONES, NOVEL HETEROCYCLES

被引：26

作者：

ADAM, W ^{[1
]}

ALBERT, R ^{[1
]}

GRAU, ND ^{[1
]}

HASEMANN, L ^{[1
]}

NESTLER, B ^{[1
]}

PETERS, EM ^{[1
]}

PETERS, K ^{[1
]}

PRECHTL, F ^{[1
]}

VONSCHNERING, HG ^{[1
]}

机构：

[1] MAX PLANCK INST FESTKORPERFORSCH,W-7000 STUTTGART,GERMANY

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1991年 / 56卷 / 20期

关键词：

D O I：

10.1021/jo00020a016

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Triphenylphosphine deoxygenation of beta-alkyl, beta,beta-dialkyl-, and beta,beta-spirocycloalkyl-substituted alpha-methylene-beta-peroxy lactones 3a-k, which are readily available by photooxygenation of the corresponding alpha,beta-unsaturated carboxylic acids 1, and cyclization of the resulting alpha-methylene-beta-hydroperoxy acids 2 constitute a convenient method for the preparation of a variety of alpha-methylene beta-lactones 5. Alternatively, the alpha-methylene-beta-hydroxy carboxylic acids 4 can be directly cyclized by benzenesulfonyl chloride in pyridine into these novel four-membered ring heterocycles 5.

引用

页码：5778 / 5781

页数：4

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