Stereoselective synthesis of di- and monofluoromethylated vicinal ethylenediamines with di- and monofluoromethyl sulfones

被引：48

作者：

Liu, Jun ^{[1
]}

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：

JOURNAL OF ORGANIC CHEMISTRY | 2007年 / 72卷 / 08期

关键词：

D O I：

10.1021/jo070094w

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The diastereoselective nucleophilic (phenylsulfonyl)difluoromethylation and (phenylsulfonyl)monofluoromethylation of alpha-amino N-tert-butanesulfinimines (3) by using PhSO2CF2H and PhSO2CH2F reagents gave products 4 or 5 in high yields (73-99%) and with excellent diastereoselectivity (dr up to > 99:1). After subsequent reductive desulfonylation and acid-catalyzed alcoholysis, compounds 4 and 5 could be readily transformed to chiral alpha-difluoromethylated or alpha-monofluoromethylated ethylenediamines in good yields.

引用

页码：3119 / 3121

页数：3

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