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Petasis-Type gem-Difluoroallylation Reactions Assisted by the Neighboring Hydroxyl Group in Amines
Xing Yang1, Ze-Hun Cao1, Yang Zhou1
1Department of Chemistry, School of Chemistry, Chemical Engineering and Life Science , Wuhan University of Technology , Wuhan 430070 , P.R. China.
Abstract:
A three-component Petasis-type gem-difluoroallylation reaction of using pinacol gem-difluoroallylboronates, aldehydes or isatin, and β-amino alcohols enabled by the neighboring hydroxyl group in amine is reported, affording various racemic and chiral gem-difluorohomoallylamine derivatives with good to excellent results. Based on the control experiment and stereochemistry of the product, a proposed reaction pathway is illustrated to clarify the origin of regio- and stereoselectivity under protic solvent conditions.
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