4.7 Article

Oxidative Heck Reaction of Glycals and Aryl Hydrazines: A Palladium-Catalyzed C-Glycosylation

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 78, Issue 17, Pages 8821-8825

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jo401032r

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Funding

  1. Nanyang Technological University [RG50/08]
  2. Ministry of Education, Singapore [MOE 2009-T2-1-030]

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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 alpha-C-glycosides were obtained when (3R)-glycals were employed, whereas alpha,beta mixtures were observed with (3S)-glycals.

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