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Syntheses of the enantiomers of 1-deoxynojirimycin and 1-deoxyaltronojirimycin via chemo- and diastereoselective olefinic oxidation of unsaturated amines.

Abstract:

Oxidation of enantiomerically pure (R)-N(1)-1'-(1''-naphthyl)ethyl-2,7-dihydro-1H-azepine with m-CPBA in the presence of HBF(4) and BnOH gave (3S,4R,5S,6S,1'R)-N(1)-1'-(1''-naphthyl)ethyl-3-hydroxy-4-benzyloxy-5,6-epoxyazepane as the major product and as a single diastereoisomer after chromatography. Elaboration of this highly functionalized intermediate via ring contraction to (2S,3R,4S,5S,1'R)-N(1)-benzyl-2-chloromethyl-3-benzyloxy-4,5-epoxypiperidine followed by regioselective epoxide ring...

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Publication status:
Published

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Publisher copy:
10.1021/jo101756g

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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:
75
Issue:
23
Pages:
8133-8146
Publication date:
2010-12-05
DOI:
EISSN:
1520-6904
ISSN:
0022-3263
URN:
uuid:a2c70645-c26b-49c7-9f0b-bd1df393f3fe
Source identifiers:
110642
Local pid:
pubs:110642

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