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A range of substituted aryl epoxides undergo efficient ring-opening hydrofluorination upon treatment with 0.33 equiv of BF(3) x OEt(2) in CH(2)Cl(2) at -20 degrees C to give the corresponding syn-fluorohydrins, consistent with a mechanism involving a stereoselective S(N)1-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 beta-fluoroamphetamines.

Original publication

DOI

10.1021/ol100862s

Type

Journal article

Journal

Org Lett

Publication Date

02/07/2010

Volume

12

Pages

2936 - 2939

Keywords

Amphetamine, Benzyl Compounds, Crystallography, X-Ray, Models, Molecular, Molecular Structure, Stereoisomerism