BCl3- and TiCl4-mediated reductions of beta-hydroxy ketones

被引：45

作者：

Sarko, CR ^{[1
]}

Collibee, SE ^{[1
]}

Knorr, AL ^{[1
]}

DiMare, M ^{[1
]}

机构：

[1] UNIV CALIF SANTA BARBARA,DEPT CHEM,SANTA BARBARA,CA 93106

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1996年 / 61卷 / 03期

关键词：

D O I：

10.1021/jo951549x

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Syn-selective reduction protocols for beta-hydroxy ketones are described exploiting the intermediacy of titanium and boron chelates derived from TiCl4 and BCl3, respectively, Reductions are conducted at -78 degrees C in CH2Cl2 using a wide range of CH2Cl2-soluble reducing agents, Added acid-scavenging agents are detrimental to reaction selectivity, An A((1,3))-like interaction involving the stereocenter responsible for asymmetric induction provides conformational biasing of the intermediate chelates necessary for high diastereoselectivity.

引用

页码：868 / 873

页数：6

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