STEREOSELECTIVE SYNTHESIS OF ALPHA,BETA-TRANS-SPIRO-BETA-LACTONES BY DIELS-ALDER CYCLOADDITION OF 1,3-DIENES TO ALPHA-METHYLENE-BETA-LACTONE AND THEIR DECARBOXYLATION BY PYROLYSIS TO (E)-ALKYLIDENECYCLOALKENES, A CONVENIENT OLEFINATION METHOD

被引：14

作者：

ADAM, W ^{[1
]}

SALGADO, VON ^{[1
]}

PETERS, EM ^{[1
]}

PETERS, K ^{[1
]}

VONSCHNERING, HG ^{[1
]}

机构：

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

来源：

CHEMISCHE BERICHTE-RECUEIL | 1993年 / 126卷 / 06期

关键词：

STEREOSELECTIVITY; DIELS-ALDER REACTION; BETA-LACTONE; ALPHA-METHYLENE; SPIROLACTONES; ALKYLIDENE CYCLOALKENES; DECARBOXYLATION;

D O I：

10.1002/cber.19931260632

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A number of spiro-beta-lactones was prepared in good to excellent yields through stereoselective [4 + 2] cycloaddition of beta-isopropyl-alpha-methylene-beta-lactone (1) with acyclic, cyclic, heterocyclic and aromatic 1,3-dienes by sealed-tube reaction at moderate temperatures (50 - 130-degrees-C). Flash pyrolysis of the resulting spiro-beta-lactones 2 in the gas phase at 400-degrees-C afforded by decarboxylation exclusively the corresponding (E)-isopropylidenealkenes in high yields with retention of the initial geometry and without double bond isomerization. This olefination method constitutes an excellent stereoselective synthesis of (E)-alkylidenecycloalkenes.

引用

页码：1481 / 1486

页数：6

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