Diastereoselective Metal‐Catalyzed Synthesis of  C ‐Aryl and  C ‐Vinyl Glycosides | Zendy

Nicolas Lionel | Zendy; Angibaud Patrick | Zendy; Stansfield Ian | Zendy; Bonnet Pascal | Zendy; Meerpoel Lieven | Zendy; Reymond Sébastien | Zendy; Cossy Janine | Zendy

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Diastereoselective Metal‐Catalyzed Synthesis of C ‐Aryl and C ‐Vinyl Glycosides

Author(s) -

Nicolas Lionel,

Angibaud Patrick,

Stansfield Ian,

Bonnet Pascal,

Meerpoel Lieven,

Reymond Sébastien,

Cossy Janine

Publication year - 2012

Publication title -

angewandte chemie international edition

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 1433-7851

DOI - 10.1002/anie.201204786

Subject(s) - aryl , cobalt , catalysis , selectivity , chemistry , glycoside , organic chemistry , reagent , medicinal chemistry , combinatorial chemistry , alkyl

Cobalt, the catalyst of choice : The diastereoselective cobalt‐catalyzed cross‐coupling of 1‐bromo glycosides and aryl or vinyl Grignard reagents is described. A convenient and inexpensive catalyst, [Co(acac) 3 ]/tmeda (acac=acetylacetonate, tmeda= N , N ′‐tetramethylethylenediamine), gives full α selectivity in the mannose and galactose series, and an α selectivity in the glucose series with α / β ratios of 1.3:1–3:1.

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