LITHIATED 5-TOSYLPROPANAL AND 4-TOSYL-2-BUTANONE DIMETHYL ACETALS AS BETA-ACYLVINYL ANION EQUIVALENTS FOR THE SYNTHESIS OF UNSATURATED 1,4-DICARBONYL COMPOUNDS AND ALPHA,BETA-BUTENOLIDES

被引：27

作者：

BONETE, P ^{[1
]}

NAJERA, C ^{[1
]}

机构：

[1] UNIV ALICANTE,DEPT QUIM ORGAN,E-03080 ALACANT,SPAIN

来源：

TETRAHEDRON | 1995年 / 51卷 / 09期

关键词：

D O I：

10.1016/0040-4020(95)00026-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The lithiation of 1,1-dimethoxy-3-tosylpropane (7a) and 2,2-dimethoxy-4-tosylbutane (7b) followed by reaction with acyl chlorides affords, after p-toluenesulfinic acid elimination, ene-1,4-dicarbonyl compounds in a stereoselective manner. In the case of compound 7a, derived from acrolein, sequential monolithiation and reaction with carbonyl compounds give cyclic acetals, which after oxidation and elimination of p-toluenesulfinic acid are transformed into alpha,beta-butenolides.

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页码：2763 / 2776

页数：14

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