title: Michael reactions on conformationally flexible methyl 3-C-nitro-hex-2-enopyranoside derivatives.
abstract: Dimethyl malonate and dibenzoylmethane attacked the C-2 position of the title 3-nitro-2-enopyranosides from the side opposite the anomeric methoxyl group to afford the 3-enopyranosides (S(N)2' products). In the case of 2,4-pentanedione and ethyl acetoacetate, further intramolecular cyclization occurred to yield dihydropyran derivatives.
authors.affiliation: Faculty of Science, Yokohama City University, Seto, Yokohama, Japan.
authors.forename: T
authors.initials: T
authors.lastname: Sakakibara
authors.forename: K
authors.initials: K
authors.lastname: Tokuda
authors.forename: T
authors.initials: T
authors.lastname: Hayakawa
authors.forename: A
authors.initials: A
authors.lastname: Seta
mesh_terms: D002236:Carbohydrate Conformation; D006027:Glycosides / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D009574:Nitro Compounds / Q000737:chemistry*; D018583:Pliability
chemical_list: D006027:Glycosides; D009574:Nitro Compounds