Stereoselective difluoromethylenation using Me3SiCF2SPh:: Synthesis of chiral 2,4-disubstituted 3,3-difluoropyrrolidines

被引：95

作者：

Li, Ya ^{[1
]}

Hu, Jinbo ^{[1
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Organofluorine Chem, Shanghai 200032, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2007年 / 46卷 / 14期

关键词：

enantioselectivity; fluoroalkylation; pyrrolidines; radical reactions; synthetic methods;

D O I：

10.1002/anie.200604783

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A radical synthon: Nucleophilic (phenylthio)difluoromethylation of (R)-N-(tert-butylsulfinyl)imines with 1, a difluoromethylene radical anion equivalent, afforded the corresponding products in good yields and with high diastereoselectivity (d.r. ≥ 98:2). The resulting PhSCF2- containing sulfinamides can be further transformed into chiral 2,4-trans-disubstituted 3,3-difluoropyrrolidines through an intramolecular radical cyclization methodology. (Chemical Equation Presented). © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：2489 / 2492

页数：4

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