title: One-pot Mukaiyama type carbon-Ferrier rearrangement of glycals: Application in the synthesis of chromanone 3-C-glycosides.
abstract: One-pot carbon-Ferrier rearrangement of glycals with unactivated aryl methyl ketones has been developed under mild Silyl triflate catalysis. Keto methyl group of various aryl methyl ketones without being converted into silyl enol ether could directly attack anomeric position of glycals to form keto functionalized C-glycosides in moderate to good yields with high α-selectivity. The versatility of this method has been extended to the synthesis of a small library of chromanone 3-C-glycosides.
authors.affiliation: Natural Product Chemistry Division, Indian Institute of Integrative Medicine, Jammu, 180001, India; CSIR, Academy of Scientific and Innovative Research, India.
authors.forename: Ashutosh K
authors.initials: AK
authors.lastname: Dash
authors.affiliation: Natural Product Chemistry Division, Indian Institute of Integrative Medicine, Jammu, 180001, India; CSIR, India.
authors.forename: Tatina
authors.initials: T
authors.lastname: Madhubabu
authors.affiliation: CSIR, India; Natural Product Chemistry Division, Indian Institute of Integrative Medicine, Kashmir, 180001, India.
authors.forename: Syed Khalid
authors.initials: SK
authors.lastname: Yousuf
authors.affiliation: Natural Product Chemistry Division, Indian Institute of Integrative Medicine, Jammu, 180001, India; CSIR, India.
authors.forename: Sushil
authors.initials: S
authors.lastname: Raina
authors.affiliation: Natural Product Chemistry Division, Indian Institute of Integrative Medicine, Jammu, 180001, India; CSIR, Academy of Scientific and Innovative Research, India. Electronic address: dmukherjee@iiim.ac.in.
authors.forename: Debaraj
authors.initials: D
authors.lastname: Mukherjee
mesh_terms: D002244:Carbon / Q000737:chemistry*; D002384:Catalysis; D002839:Chromans / Q000737:chemistry*; D006027:Glycosides; D006031:Glycosylation; D015394:Molecular Structure; D009005:Monosaccharides / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: C438934:C-glycoside; D002839:Chromans; D006027:Glycosides; D009005:Monosaccharides; D002244:Carbon
keywords: 2,3-Unsaturated glycosides; Acetophenones; Carbon-Ferrier rearrangement; Chromanone 3-C-glycosides; Glycopyranosides; Lewis acid