Beta-fluoroamphetamines via the stereoselective synthesis of benzylic fluorides.

Symplectic ID: 
58619
Source: 
PubMed
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1
Last Synced with Symplectic: 
Monday, 14 September, 2026 - 23:25
DOI: 
10.1021/ol100862s
Publication Date: 
Friday, 2 July, 2010
First Page: 
2936
Last Page: 
2939
Keywords: 
Amphetamine
Benzyl Compounds
Crystallography, X-Ray
Models, Molecular
Molecular Structure
Stereoisomerism
Authors: 
Cresswell, AJ
Davies, SG
Lee, JA
Roberts, PM
Russell, AJ
Thomson, JE
Tyte, MJ
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0
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Abstract: 
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.
Journal Title: 
Org Lett
eISSN: 
1523-7052
Volume: 
12
Issue: 
13
ID at Source: 
20509635
Publication Status: 
Published
Open access: 
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