A SELECTIVITY STUDY OF ACTIVATED KETAL REDUCTION WITH BORANE DIMETHYL SULFIDE

被引：36

作者：

BARTELS, B ^{[1
]}

HUNTER, R ^{[1
]}

机构：

[1] UNIV CAPE TOWN,DEPT CHEM,RONDEBOSCH 7700,SOUTH AFRICA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1993年 / 58卷 / 24期

关键词：

D O I：

10.1021/jo00076a041

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A chemo- and regioselectivity study of the reagent combination BH3.SMe2/TMSOTf for ketal reduction has been undertaken. It has revealed that simple 1,3-dioxanes reduce cleanly at low temperature in CH2Cl2 while simple 1,3-dioxolanes may give complete ring cleavage and dimerization products. A study of reduction of 4-substituted 1,3-dioxolanes has revealed a solvent-directed regioselectivity which in THF favors the secondary protected derivative. A mechanism is postulated to account for the selectivities based on recent thinking on acetal substitution reactions.

引用

页码：6756 / 6765

页数：10

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