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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.