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

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

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 dif...

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Bibliographic Details
Published in:Journal of the American Chemical Society Vol. 134; no. 41; pp. 16999 - 17002
Main Authors: Shen, Xiao, Zhang, Wei, Ni, Chuanfa, Gu, Yucheng, Hu, Jinbo
Format: Journal Article
Language:English
Published: United States American Chemical Society 17-10-2012
Subjects:
Hydrocarbons, Fluorinated - chemistry
Imines - chemistry
Ketones - chemistry
Methylation
Molecular Structure
Stereoisomerism
Online Access:Get full text
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Summary: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.
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ISSN:0002-7863
1520-5126
DOI:10.1021/ja308419a