Oxidative Heck reaction of glycals and aryl hydrazines: a palladium-catalyzed C-glycosylation.

J Org Chem

Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371.

Published: September 2013

An efficient Heck-type C-glycosylation of glycals via the C-N bond cleavage of aryl hydrazines has been developed. The flexibility of the reaction was tested by the substrate scope, consisting of glycals from different carbohydrate origins as well as aryl hydrazines with various substituents. Pure α-C-glycosides were obtained when (3R)-glycals were employed, whereas α,β mixtures were observed with (3S)-glycals.

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http://dx.doi.org/10.1021/jo401032rDOI Listing

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