Iridium-Catalyzed Enantioselective Fluorination of Racemic, Secondary Allylic Trichloroacetimidates

The Ir-catalyzed enantioselective fluorination of racemic, branched allylic trichloroacetimidates with Et3N·3HF is a mild and efficient route for selective incorporation of fluoride ion into allylic systems. We herein describe the asymmetric fluorination of racemic, secondary allylic electrophiles w...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2015-09, Vol.137 (37), p.11912-11915
Main Authors: Zhang, Qi, Stockdale, David P, Mixdorf, Jason C, Topczewski, Joseph J, Nguyen, Hien M
Format: Article
Language:English
Subjects:
Acetamides - chemistry
Catalysis
Chloroacetates - chemistry
Halogenation
Iridium - chemistry
Models, Molecular
Molecular Conformation
Stereoisomerism
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Summary:The Ir-catalyzed enantioselective fluorination of racemic, branched allylic trichloroacetimidates with Et3N·3HF is a mild and efficient route for selective incorporation of fluoride ion into allylic systems. We herein describe the asymmetric fluorination of racemic, secondary allylic electrophiles with Et3N·3HF using a chiral-diene-ligated Ir complex. The methodology enables the formation of acyclic fluorine-containing compounds in good yields with excellent levels of asymmetric induction and overcomes the limitations previously associated with the enantioselective construction of secondary allylic fluorides bearing α-linear substituents.
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.5b07492