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Indium‐Promoted Barbier‐Type Allylations in Aqueous Media: New Access to 2‐ C ‐ and 4‐ C ‐Branched Sugars
Author(s) -
Lubineau André,
Canac Yves,
Le Goff Nicole
Publication year - 2002
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/1615-4169(200206)344:3/4<319::aid-adsc319>3.0.co;2-s
Subject(s) - chemistry , aqueous medium , indium , aqueous solution , sugar , organic chemistry , combinatorial chemistry
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.