Highly stereocontrolled synthesis of substituted propiolactones and butyrolactones from achiral lithium enolates and homochiral aldehydes

被引:35
作者
Arrastia, I
Lecea, B
Cossio, FP
机构
[1] EUSKAL HERRIKO UNIBERTSITATEA,KIRNIKA FAK,E-20080 SAN SEBASTIAN,SPAIN
[2] EUSKAL HERRIKO UNIBERTSITATEA,FARMAZI FAK,E-01080 VITORIA,SPAIN
关键词
D O I
10.1016/0040-4039(95)02139-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Lithium enolates derived from achiral thiol esters react in a highly stereoselective fashion with homochiral aldehydes to yield the corresponding 2-oxetanones. The stereochemical outcome of the reaction corresponds to a non-chelation control, except when O-silylated mandelaldehyde is used. The propiolactones thus formed are efficiently transformed into delta-lactones via Lewis acid promoted dyotropic rearrangements.
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页码:245 / 248
页数:4
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