Journal article icon

Journal article

Beta-fluoroamphetamines via the stereoselective synthesis of benzylic fluorides.

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.
Publication status:
Published

Actions


Access Document


Publisher copy:
10.1021/ol100862s

Authors


More by this author
Institution:
University of Oxford
Division:
MPLS
Department:
Chemistry
Sub department:
Organic Chemistry
Role:
Author
Journal:
Organic letters More from this journal
Volume:
12
Issue:
13
Pages:
2936-2939
Publication date:
2010-07-01
DOI:
EISSN:
1523-7052
ISSN:
1523-7060
Language:
English
Keywords:
Pubs id:
pubs:58619
UUID:
uuid:b8460aac-e692-4272-956c-3469f466141c
Local pid:
pubs:58619
Source identifiers:
58619
Deposit date:
2012-12-19

Terms of use


Views and Downloads






If you are the owner of this record, you can report an update to it here: Report update to this record

TO TOP