Stereoselective synthesis of substituted 1,2-annulated sugars by domino double-Michael addition reaction

A simple, highly stereoselective one-pot methodology for the synthesis of novel 1,2-annulated sugars comprising of oxa-oxa and oxa-carbasugar fused skeletons from 2-nitrogalactal and a sugar-derived enone, obtained from 2-formylgalactal, promoted by KOtBu and CH3ONa respectively is described. Both p...

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Bibliographic Details
Published in:Carbohydrate research 2019-05, Vol.477, p.26-31
Main Authors: Parasuraman, Kadigachalam, Chennaiah, Ande, Dubbu, Sateesh, Ibrahim Sheriff, A.K., Vankar, Yashwant D.
Format: Article
Language:English
Subjects:
1,2-Annulated sugars
2-Nitrogalactal
Domino double-Michael addition reaction
Sugar-derived dienone
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Summary:A simple, highly stereoselective one-pot methodology for the synthesis of novel 1,2-annulated sugars comprising of oxa-oxa and oxa-carbasugar fused skeletons from 2-nitrogalactal and a sugar-derived enone, obtained from 2-formylgalactal, promoted by KOtBu and CH3ONa respectively is described. Both processes rely on a domino double-Michael addition reaction resulting in the formation of three stereocenters in a single pot, including a quaternary center. [Display omitted] •Domino double-Michael addition was explored in the synthesis of 1,2-annulated sugars.•2-nitrogalactal and C2-formyl galactal derived dienones were used as synthons.•1,2-annulated sugars with oxa-oxa as well as oxa-carbasugar skeletons were prepared.
ISSN:0008-6215
1873-426X
DOI:10.1016/j.carres.2019.03.007