1,2-STEREOINDUCTION IN RADICAL REACTIONS - STEREOSELECTIVE SYNTHESIS OF 2-ALKYL-3-HYDROXYBUTANOATES

被引：32

作者：

BULLIARD, M ^{[1
]}

ZEHNDER, M ^{[1
]}

GIESE, B ^{[1
]}

机构：

[1] UNIV BASEL,DEPT CHEM,ST JOHANNS RING 19,CH-4056 BASEL,SWITZERLAND

来源：

HELVETICA CHIMICA ACTA | 1991年 / 74卷 / 07期

关键词：

D O I：

10.1002/hlca.19910740722

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Radical addition to 2-cyclohexyl-5-methylidene-6-methyl-1,3-dioxan-4-one (2) affords stereoselectively 5,6-trans-products trans-3. The size of the radical has no influence on the selectivity. These trans-acetals are converted into threo-3-hydroxy-butanoates 4. Methyl 2-methylidene-3-[(tert-butyl)diphenylsilyloxy]butanoate (5), treated under the same conditions, leads mainly to the erythro-isomer of 4 after deprotection. An influence of the steric bulkyness of the radical is observed. The stereochemical course of the reactions is discussed.

引用

页码：1600 / 1607

页数：8

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