BETA-VINYL-GAMMA-BUTYROLACTONES VIA THE PALLADIUM-CATALYZED REACTION OF VINYL TRIFLATES WITH Z-2-BUTEN-1,4-DIOL

被引：33

作者：

ARCADI, A

BERNOCCHI, E

CACCHI, S

MARINELLI, F

机构：

[1] UNIV LAQUILA,DIPARTIMENTO CHIM INGN CHIM MAT,VIA ASSERGI 4,I-67100 LAQUILA,ITALY

[2] UNIV ROMA LA SAPIENZA,DIPARTIMENTO CHIM & TECNOL SOSTANZE BIOLOGICAMENTE ATTIVE,I-00185 ROME,ITALY

来源：

TETRAHEDRON | 1991年 / 47卷 / 08期

关键词：

D O I：

10.1016/S0040-4020(01)86427-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The palladium-catalysed reaction of vinyl triflates with Z-2-buten-1,4-diol affords beta-vinyl-gamma-butyrolactols (4-vinyl-2-hydroxy-tetrahydrofurans) which are converted into the corresponding beta-vinyl-gamma-butyrolactones by a smooth oxidation with Ag2CO3 on celite. Preparation of beta-substituted-gamma-butyrolactones can be performed without the isolation of the intermediate gamma-butyrolactols, thus simplifying the procedure and usually with higher overall yields. The outcome of the palladium-catalysed formation of beta-substituted-gamma-butyrolactols strongly depends on the nature of the added base. Best results are obtained by using NaHCO3 or K2CO3 in the presence of n-Bu4NCl or TEBA.

引用

页码：1525 / 1540

页数：16

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