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Synfacts 2007(7): 0756-0756  
DOI: 10.1055/s-2007-968629
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart · New York

Enantioselective Monofluoromethylation Reaction

Contributor(s): Benjamin List, Sebastian Hoffmann
S. Mizuta, N. Shibata*, Y. Goto, T. Furukawa, S. Nakamura, T. Toru*
Nagoya Institute of Technology, Japan
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Publication History

Publication Date:
22 June 2007 (online)

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Significance

A quaternary ammonium salt catalyzed enantioselective monofluoromethylation based on fluorobis(phenylsulfonyl)methane 3 chemistry provides efficient access to α-mono­fluoromethylated amines 5. Initially, electrophilic prochiral imines 2 are generated in situ from α-amido sulfones 1 via desulfonylation which then react with 3 in the presence of cinchona alkaloid derived phase-transfer catalyst 6. Very good yields and enantioselectivities were observed in dichloro­methane at -80 °C. Products 4 could be further converted into α-monofluoromethylamines 5 by reductive removal of the two phenylsulfonyl groups.