期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 74, 期 3, 页码 1200-1204出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo802378s
关键词
-
资金
- DGICYT [CTQ2006-06741]
- Comunidad Autonoma de Madrid [CCG07-UAM/PPQ-1849]
- Comunidad Autonoma de Madrid
The efficiency of the sulfinyl group as a remote controller of the chemoselectivity and diastereoselectivity of the reduction of alpha,beta-unsaturated alpha-[2-(p-tolylsulfinyl)phenyl] substituted ketones 1 has been demonstrated in reactions carried out under NaBH4 in the presence of Yb(OTf)(3) as the chelating agent. The starting unsaturated ketones have been prepared from the corresponding 2-(p-tolylsulfinyl) benzyl alkyl (and aryl) ketones 2 by insertion of the methylidene group under modified Mannich conditions, exploiting ultrasound irradiation to obtain the aminomethylation adducts and silica gel treatment to produce its complete elimination. Desulfinylation of the reduction products yielded the corresponding vinyl carbinols with high enantiomeric purity.
作者
我是这篇论文的作者
点击您的名字以认领此论文并将其添加到您的个人资料中。
推荐
暂无数据