【Org.Lett】氟化学最新进展1.pdfVIP

ORGANIC LETTERS -Fluoroamphetamines via the XXXX Vol. xx, No. x Stereoselective Synthesis of Benzylic Fluorides Alexander J. Cresswell,† Stephen G. Davies,*,† James A. Lee,† Paul M. Roberts,† Angela J. Russell,† James E. Thomson,† and Melloney J. Tyte‡ Department of Chemistry, Chemistry Research Laboratory, Uni Versity of Oxford, Mansfield Road, Oxford OX1 3TA, U.K., and Syngenta, Jealott’s Hill International Research Centre, Bracknell, Berkshire RG42 6EY, U.K. steVe.daVies@chem.ox.ac.uk Received April 15, 2010 ABSTRACT A range of substituted aryl epoxides undergo efficient ring-opening hydrofluorination upon treatment with 0.33 equiv of BF ·OEt in CH Cl at 3 2 2 2 -20 °C to give the corresponding syn-fluorohydrins, consistent with a mechanism involving a stereoselective SN1-type epoxide ring-opening process. The benzylic fluoride products of these reactions are valuable templates for further elaboration, as demonstrated by the preparation of a range of aryl-substituted -fluoroamphetamines. The incorporation of fluorine into organic molecules frequently applicable methods for the stereoselective synthesis of this class has a dramatic impact on their physical, chemical, and biological