title: Tandem regio- and diastereo-selective synthesis of halogenated C-vinyl glycosides from unactivated arylacetylenes.
abstract: A highly regio- and diastereo-selective synthesis of halogenated C-vinyl glycosides has been achieved from glycals and unactivated aryl acetylenes in the presence of halogenated Lewis acids via a tandem glycosylation-halogenation reaction. The Lewis acid used served the dual purpose of activating the allylic acetoxy group of glycals and serving as halogen source for Markovnikov addition across the triple bond, which makes the process atom economic. The synthesized glycosyl vinyl halides have been used as precursors for various Pd catalyzed C-C cross coupling reactions.
authors.affiliation: Academy of Scientific and Innovative Research, CSIR-IIIM, India. dmukherjee@iiim.ac.in.
authors.forename: Madhubabu
authors.initials: M
authors.lastname: Tatina
authors.forename: Anil Kumar
authors.initials: AK
authors.lastname: Kusunuru
authors.forename: Syed Khalid
authors.initials: SK
authors.lastname: Yousuf
authors.forename: Debaraj
authors.initials: D
authors.lastname: Mukherjee
mesh_terms: D000114:Acetylene / Q000031:analogs & derivatives* / Q000737:chemistry; D000480:Alkynes / Q000737:chemistry; D002244:Carbon / Q000737:chemistry; D002384:Catalysis; D006027:Glycosides / Q000138:chemical synthesis / Q000737:chemistry*; D006031:Glycosylation; D054879:Halogenation; D058116:Lewis Acids / Q000737:chemistry; D010165:Palladium / Q000737:chemistry; D013237:Stereoisomerism; D014753:Vinyl Compounds / Q000737:chemistry*
chemical_list: D000480:Alkynes; D006027:Glycosides; D058116:Lewis Acids; D014753:Vinyl Compounds; C044736:phenylacetylene; D010165:Palladium; D002244:Carbon; D000114:Acetylene