Tuning the Reactivity of Difluoromethyl Sulfoximines from Electrophilic to Nucleophilic: Stereoselective Nucleophilic Difluoromethylation of Aryl Ketones

被引：126

作者：

Shen, Xiao ^{[1
]}

Zhang, Wei ^{[1
]}

Ni, Chuanfa ^{[1
]}

Gu, Yucheng ^{[2
]}

Hu, Jinbo ^{[1
]}

机构：

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

[2] Syngenta Jealotts Hill Int Res Ctr, Bracknell RG42 6EY, Berks, England

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2012年 / 134卷 / 41期

基金：

中国国家自然科学基金;

关键词：

ESSENTIAL OIL; CARBONYL-COMPOUNDS; TRIFLUOROMETHYLATION; INHIBITORS; FLUORINE; PERFLUOROALKYLATION; IDENTIFICATION; DERIVATIVES; ANALOGS; REAGENT;

D O I：

10.1021/ja308419a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A stereoselective synthesis of enantiomerically enriched difluoromethyl tertiary alcohols by tuning the reactivity of difluoromethyl sulfoximines from electrophilic to nucleophilic difluoromethylating agents is reported. The key feature of this chemistry is the diastereoselective addition of the difluoromethyl sulfoximine to the prochiral carbon of the ketone. The present method was used to prepare enantiomerically enriched difluoromethyl secondary alcohols and difluorinated analogues of the natural products gossonorol and boivinian B, demonstrating the potency of the method.

引用

页码：16999 / 17002

页数：4

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