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

André Lubineau (1) , Yves Canac (1) , Nicole Le Goff (1)

1 GM - Glycochimie moléculaire

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.

Mots clés: Aqueous media; Barbier reaction; C-branched sugar; C-C coupling; Indium

Domaines: Chimie de coordination

André Lubineau, Yves Canac, Nicole Le Goff. Indium-Promoted Barbier-Type Allylations in Aqueous Media: New Access to 2-C- and 4-C-Branched Sugars. Advanced Synthesis and Catalysis, 2002, 344 (3-4), pp.319-327. ⟨10.1002/1615-4169(200206)344:3/4<319::AID-ADSC319>3.0.CO;2-S⟩. ⟨hal-03739756⟩