SYNTHESIS OF GAMMA-LACTONES AND DELTA-LACTONES BY FREE-RADICAL ANNELATION OF SE-PHENYL SELENOCARBONATES

被引：82

作者：

BACHI, MD

BOSCH, E

机构：

[1] Department of Organic Chemistry, The Weizmann Institute Of Science

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1992年 / 57卷 / 17期

关键词：

D O I：

10.1021/jo00043a030

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A general method for the synthesis of gamma- and delta-lactones through the intramolecular addition of alkoxycarbonyl radicals, formed by reaction of Se-phenylselenocarbonates with n-Bu3SnH, onto carbon-carbon multiple bonds is described. This free-radical cyclization is characterized by high regioselectivity favoring exo addition and by a high ratio of cyclization to reduction. Monocyclic, fused bicyclic, and spirocyclic lactones are formed in good to excellent yield. Use of allyltri-n-butyltin as a chain-transfer agent in the place of n-Bu3SnH affords the corresponding 3-butenyl lactones.

引用

页码：4696 / 4705

页数：10

共 41 条

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[2]

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[3]

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