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Stereoselective Nucleophilic Fluoromethylation of Aryl Ketones: Dynamic Kinetic Resolution of Chiral α‐Fluoro Carbanions
Author(s) -
Shen Xiao,
Miao Wenjun,
Ni Chuanfa,
Hu Jinbo
Publication year - 2014
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201308484
Subject(s) - carbanion , nucleophile , kinetic resolution , chemistry , stereoselectivity , aryl , tertiary alcohols , selectivity , combinatorial chemistry , nucleophilic substitution , computational chemistry , organic chemistry , catalysis , enantioselective synthesis , alkyl
Although many methods are available for the synthesis of optically enriched monofluoromethyl secondary alcohols, synthesizing optically enriched monofluoromethyl tertiary alcohols remains a challenge. An efficient and easy‐to‐handle nucleophilic fluoromethylation protocol was developed. The current monofluoromethylation showed much higher facial selectivity than the corresponding difluoromethylation and proceeded via a different type of transition state. Excellent stereoselective control at the fluorinated carbon chiral center was found, an effect believed to be facilitated by the dynamic kinetic resolution of the chiral α‐fluoro carbanions.