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Asymmetric syntheses of 2,5-dideoxy-2,5-imino-D-glucitol [(+)-DGDP] and 1,2,5-trideoxy-1-amino-2,5-imino-D-glucitol [(+)-ADGDP]

Abstract:

The asymmetric syntheses of 2,5-dideoxy-2,5-imino-d-glucitol [(+)-DGDP] and 1,2,5-trideoxy-1-amino-2,5-imino-d-glucitol [(+)-ADGDP] were achieved via the ring-closing iodoamination of an enantiopure bishomoallylic amine, followed by functionalisation of the resultant iodomethyl substituted pyrrolidine. In the case of (+)-DGDP, formation of the corresponding aziridinium ion followed by regioselective ring-opening with HO gave the desired hydroxymethyl substituted pyrrolidine as a single diaste...

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Publication status:
Published

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Publisher copy:
10.1016/j.tet.2014.03.100

Authors


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Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Figuccia, ALA More by this author
Fletcher, AM More by this author
Roberts, PM More by this author
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Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Journal:
TETRAHEDRON
Volume:
70
Issue:
22
Pages:
3601-3607
Publication date:
2014-06-03
DOI:
EISSN:
1464-5416
ISSN:
0040-4020
URN:
uuid:cd297172-2595-4eab-8f6f-66429e979ec6
Source identifiers:
463663
Local pid:
pubs:463663

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