Enantioselective syntheses of substituted γ-butyrolactones

被引：14

作者：

Eliel, EL ^{[1
]}

Bai, X ^{[1
]}

Ohwa, M ^{[1
]}

机构：

[1] Univ N Carolina, Dept Chem, WR Kenan Jr Labs, Chapel Hill, NC 27599 USA

来源：

JOURNAL OF THE CHINESE CHEMICAL SOCIETY | 2000年 / 47卷 / 01期

关键词：

gamma-butyrolactones; alpha-methylene-gamma-butyrolactones; 3-and; 4-hydroxy-alpha-butyrolactones;

D O I：

10.1002/jccs.200000006

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The previously described chiral 2-acyloxathianes 5 (Scheme I) are used in two different enantioselective syntheses of gamma-butyrolactones. In one synthesis, Grignard addition, cleavage and reduction to carbinols RR'C(OH)CH2OH is followed by tosylation, malonate homologation, lactonization, and removal of the carbomethoxy group to give optically active gamma-lactones. A modification of this synthesis (Scheme I) leads to optically active alpha-methyl ene-gamma-lactones. In the second synthesis, reaction of a bromomagnesium enolate with ketones 5 leads to beta-hydroxyesters, which, by appropriate sequences of reduction and cleavage (Scheme II) are converted to optically active alpha- or beta-hydroxy-gamma-lactones.

引用

页码：63 / 70

页数：8

共 48 条

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