4.8 Article

Palladium(II) acetate catalyzed stereoselective C-glycosidation of peracetylated glycals with arylboronic acids

Journal

ORGANIC LETTERS
Volume 3, Issue 13, Pages 2013-2015

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol010070q

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[GRAPHICS] Addition of a variety of arylboronic acids to peracetylated glycals takes place in the presence of a catalytic amount of Pd(OAc)(2). The reaction involves the syn addition of a sigma -aryl-Pd complex to the glycal double band followed by anti elimination of Pd(OAc)(2) to provide a carbon-ferrier type product, This method provides a practical and convenient stereoselective synthesis of C-arylglycosides.

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