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Angew Chem Int Ed Engl. 2014 Jan 13;53(3):775-9. doi: 10.1002/anie.201308484. Epub 2013 Dec 4.

Stereoselective nucleophilic fluoromethylation of aryl ketones: dynamic kinetic resolution of chiral α-fluoro carbanions.

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  • 1Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Ling-Ling Road, Shanghai, 200032 (China)


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.

Copyright © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.


alcohols; chirality; fluoromethylation; stereoselective addition; sulfoximine

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