Beta-fluoroamphetamines via the stereoselective synthesis of benzylic fluorides.
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.
Cresswell
Alexander J
AJ
Department of Chemistry, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA, UK.
Davies
Stephen G
SG
Lee
James A
JA
Roberts
Paul M
PM
Russell
Angela J
AJ
Thomson
James E
JE
Tyte
Melloney J
MJ
D000661:Amphetamine / Q000138:chemical synthesis* / Q000737:chemistry; D001593:Benzyl Compounds / Q000737:chemistry*; D018360:Crystallography, X-Ray; D008958:Models, Molecular; D015394:Molecular Structure; D013237:Stereoisomerism
D001593:Benzyl Compounds; D000661:Amphetamine