Journal article icon

Journal article

Ring-opening hydrofluorination of 2,3- and 3,4-epoxy amines by HBF4·OEt2: application to the asymmetric synthesis of (S,S)-3-deoxy-3-fluorosafingol.

Abstract:
Treatment of a range of 2,3- and 3,4-epoxy amines with HBF(4)·OEt(2) at room temperature results in fast and efficient S(N)2-type ring-opening hydrofluorination to give stereodefined amino fluorohydrins. Operational simplicity, scalability, and short reaction time at ambient temperature are notable features of this method. The utility of this methodology is exemplified in a concise asymmetric synthesis of (S,S)-3-deoxy-3-fluorosafingol.
Publication status:
Published

Actions


Access Document


Publisher copy:
10.1021/jo200517w

Authors


More by this author
Institution:
University of Oxford
Division:
MPLS
Department:
Chemistry
Sub department:
Organic Chemistry
Role:
Author
Expand authors...
Journal:
Journal of organic chemistry
Volume:
76
Issue:
11
Pages:
4617-4627
Publication date:
2011-06-01
DOI:
EISSN:
1520-6904
ISSN:
0022-3263
Source identifiers:
138784
Language:
English
Pubs id:
pubs:138784
UUID:
uuid:52763eb7-7f58-4a50-a130-1d2e86ff8448
Local pid:
pubs:138784
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