PALLADIUM(II)-CATALYZED CARBONYLATION OF 3-BUTEN-1-OLS AND 3-BUTYN-1-OLS - AN EFFICIENT SYNTHESIS OF GAMMA-BUTYROLACTONES

被引：107

作者：

TAMARU, Y ^{[1
]}

HOJO, M ^{[1
]}

YOSHIDA, Z ^{[1
]}

机构：

[1] KYOTO UNIV,FAC ENGN,DEPT SYNTHET CHEM,SAKYO KU,KYOTO 606,JAPAN

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1991年 / 56卷 / 03期

关键词：

D O I：

10.1021/jo00003a036

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Palladium(II)-catalyzed dicarbonylation of 3-buten-1-ols (1) in the presence of propylene oxide and ethyl orthoacetate in methanol-dichloromethane under carbon monoxide at atmospheric pressure afforded alpha-[(methoxycarbonyl)methyl]-gamma-butyrolactones (2) in good yields. This dicarbonylation reaction occurs via stereospecific cis addition. Under similar conditions, 4-(trimethylsilyl)-3-butyn-1-ols (4a and 4b) undergo dicarbonylation to provide cis-dicarbonylated alpha-methylene-gamma-butyrolactones (5a and 5b, respectively). 4-Alkyl-and 4-aryl-3-butyn-1-ols (4c-g), on the other hand, undergo trans alkoxycarbonylation across the triple bond and selectively furnish E tetrasubstituted alpha-methylene-gamma-butyrolactones (6).

引用

页码：1099 / 1105

页数：7

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