Difluoromethyl phenyl sulfone as a selective difluoromethylene dianion equivalent:: One-pot stereoselective synthesis of anti-2,2-difluoropropane-1,3-diols

被引：73

作者：

Prakash, GKS

Hu, JB

Mathew, T

Olah, GA

机构：

[1] Univ So Calif, Loker Hydrocarbon Res Inst, Los Angeles, CA 90089 USA

[2] Univ So Calif, Dept Chem, Los Angeles, CA 90089 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2003年 / 42卷 / 42期

关键词：

alcohols; C-C coupling; diastereoselectivity; fluorine;

D O I：

10.1002/anie.200352172

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Intramolecular charge-charge repulsion rather than traditional steric control is responsible for the high diastereoselectivity (up to 94% de) obtained in tBuOK-induced difluoromethylenation of aldehydes 1 with difluoromethyl phenyl sulfone (2) to give symmetrical and unsymmetrical anti-2,2-difluoropropane-1,3-diols 3.

引用

收藏

页码：5216 / 5219

页数：4

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