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Asymmetric Syntheses of (–)-ADMJ and (+)-ADANJ: the 2-Deoxy-2-amino Analogues of (–)-1-Deoxymannojirimycin and (+)-1-Deoxyallonojirimycin

Abstract:

The asymmetric syntheses of (–)-ADMJ and (+)-ADANJ, the 2-deoxy-2-amino analogues of (–)-1-deoxymannojirimycin and (+)-1-deoxyallonojirimycin, are described herein. Methodology for the ring-closing iodoamination of bishomoallylic amines followed by in situ ring-expansion (via intramolecular ring-opening of the corresponding aziridinium intermediates with a tethered carbamate moiety) to give oxazolidin-2-ones was initially optimised on a model system. Subsequent application of this methodology...

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Publication status:
Published
Peer review status:
Peer reviewed
Version:
Accepted manuscript

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Publisher copy:
10.1021/acs.joc.6b01107

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Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Role:
Author
More by this author
Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Role:
Author
More by this author
Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Role:
Author
More by this author
Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Role:
Author
More by this author
Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Role:
Author
Publisher:
American Chemical Society Publisher's website
Journal:
Journal of Organic Chemistry Journal website
Volume:
81
Issue:
15
Pages:
6481–6495
Publication date:
2016-06-29
DOI:
EISSN:
1520-6904
ISSN:
0022-3263
URN:
uuid:a0d832f4-9694-44cb-aa60-77de6aae293d
Source identifiers:
631638
Local pid:
pubs:631638
Paper number:
15

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