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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

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Publisher copy:
10.1021/jo200517w

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Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Role:
Author
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Journal:
The Journal of organic chemistry
Volume:
76
Issue:
11
Pages:
4617-4627
Publication date:
2011-06-05
DOI:
EISSN:
1520-6904
ISSN:
0022-3263
URN:
uuid:52763eb7-7f58-4a50-a130-1d2e86ff8448
Source identifiers:
138784
Local pid:
pubs:138784
Language:
English

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