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Diastereodivergent hydroxyfluorination of cyclic and acyclic allylic amines: synthesis of 4-deoxy-4-fluorophytosphingosines.

Abstract:

A diastereodivergent hydroxyfluorination protocol enabling the direct conversion of some conformationally biased allylic amines to the corresponding diastereoisomeric amino fluorohydrins has been developed. Sequential treatment of a conformationally biased allylic amine with 2 equiv of HBF(4)·OEt(2) followed by m-CPBA promotes epoxidation of the olefin on the face proximal to the amino group under hydrogen-bonded direction from the in situ formed ammonium ion. Regioselective and stereospecifi...

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Publication status:
Published

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Publisher copy:
10.1021/jo301056r

Authors


Cresswell, AJ More by this author
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Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Morris, MJ More by this author
Roberts, PM More by this author
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Journal:
The Journal of organic chemistry
Volume:
77
Issue:
17
Pages:
7262-7281
Publication date:
2012-09-05
DOI:
EISSN:
1520-6904
ISSN:
0022-3263
URN:
uuid:a98a71c7-7158-49f2-bd19-5ba3eb044e62
Source identifiers:
345612
Local pid:
pubs:345612

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