Indium-Promoted Barbier-Type Allylations in Aqueous Media: New Access to 2-C- and 4-C-Branched Sugars

Indium‐promoted Barbier‐type allylations in aqueous media of 2‐bromo‐4‐enopyranoside (3) and 4‐bromo‐2‐enopyranosides (2β, 6α and 6β) provide a new access to different 2‐C‐branched sugars (7, 11, 13) and 4‐C‐branched sugar (18). Moreover, apart from the synthesis and characterization of these C‐bran...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2002-06, Vol.344 (3-4), p.319-327
Main Authors: Lubineau, André, Canac, Yves, Le Goff, Nicole
Format: Article
Language:English
Subjects:
aqueous media
Barbier reaction
C-branched sugar
C-C coupling
Chemical Sciences
Coordination chemistry
indium
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Summary:Indium‐promoted Barbier‐type allylations in aqueous media of 2‐bromo‐4‐enopyranoside (3) and 4‐bromo‐2‐enopyranosides (2β, 6α and 6β) provide a new access to different 2‐C‐branched sugars (7, 11, 13) and 4‐C‐branched sugar (18). Moreover, apart from the synthesis and characterization of these C‐branched sugars, mechanistic aspects of these reactions are discussed.
ISSN:1615-4150
1615-4169
DOI:10.1002/1615-4169(200206)344:3/4<319::AID-ADSC319>3.0.CO;2-S