REGIOSELECTIVE, DIASTEREOSELECTIVE, AND ENANTIOSELECTIVE SYNTHESIS OF VIC-DIOLS VIA ALPHA-SILYL KETONES ACCORDING TO THE SAMP/RAMP HYDRAZONE METHOD

被引：35

作者：

ENDERS, D

NAKAI, S

机构：

[1] Institut Für Organische Chemie, Technischen Hochschule Aachen, Aachen

来源：

CHEMISCHE BERICHTE | 1991年 / 124卷 / 01期

关键词：

KETONES; ALPHA-SILYL; VIC-DIOLS; DIASTEREOSELECTIVE AND ENANTIOSELECTIVE SYNTHESIS; SAMP; RAMP HYDRAZONES; L-SELECTRIDE REDUCTIONS;

D O I：

10.1002/cber.19911240133

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

alpha-Silylated ketones 5 or 10 of high enantiomeric purity (ee greater-than-or-equal-to 90%) are easily available by silylation or silylation/alkylation of ketones 1 or 6, resp., according to the SAMP/RAMP hydrazone method. Reduction of 5 or 10 with L-selectride(R), followed by oxidative cleavage of the C - Si bond, leads to vic-diols 11 - 13 with high diastereoselectivity (de greater-than-or-equal-to 90%) and without racemization. The stereoselectivity of the reduction depends on the structure of the alpha-silyl ketones 5 or 10, the reducing reagents, and the solvents used.

引用

页码：219 / 226

页数：8