title: Intramolecular nitrile oxide-alkene cycloaddition of sugar derivatives with unmasked hydroxyl group(s).
abstract: [reaction: see text] Intramolecular nitrile oxide-alkene cycloaddition (INOC) of sugar derivatives with one to four free hydroxyl group(s) is reported. The INOC reaction, using chloramine-T, in the presence of silica gel, to generate nitrile oxides from oximes, proceeded smoothly to afford five- or six-membered carbocycles in good to excellent yields. This new methodology alleviates protection/deprotection steps and makes the synthetic route shorter and more efficient.
authors.affiliation: Department of Chemistry and Center of Novel Functional Molecules, The Chinese University of Hong Kong, Shatin, NT, Hong Kong, China. tonyshing@cuhk.edu.hk
authors.forename: Tony K M
authors.initials: TK
authors.lastname: Shing
authors.forename: Wai F
authors.initials: WF
authors.lastname: Wong
authors.forename: Hau M
authors.initials: HM
authors.lastname: Cheng
authors.forename: Wun S
authors.initials: WS
authors.lastname: Kwok
authors.forename: King H
authors.initials: KH
authors.lastname: So
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D002241:Carbohydrates / Q000737:chemistry*; D002700:Chloramines / Q000737:chemistry; D003500:Cyclization; D006900:Hydroxylation; D007783:Lactones / Q000737:chemistry; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry*; D010091:Oximes / Q000737:chemistry; D058428:Silica Gel; D012822:Silicon Dioxide / Q000737:chemistry; D014105:Tosyl Compounds / Q000737:chemistry
chemical_list: D000475:Alkenes; D002241:Carbohydrates; D002700:Chloramines; D007783:Lactones; D009570:Nitriles; D010091:Oximes; D014105:Tosyl Compounds; C016300:chloramine-T; D058428:Silica Gel; D012822:Silicon Dioxide