title: Regio- and stereoselectivity of the addition of O-, S-, N-, and C-nucleophiles to the beta vinyl oxirane derived from D-glucal.
abstract: 6-O-Trityl- (1a) and 6-(O-benzyl)-substituted epoxide (1b) derived from D-glucal were examined in their addition reactions with O-, C-, N-, and S-nucleophiles. A 1,4-regio- and beta-stereoselective or an anti 1,2-addition pathway is commonly observed depending on the ability of the nucleophile to coordinate with the oxirane oxygen. When TMSN(3) or LiN(3) are used as azide-based nucleophiles, a 1,2-syn-addition pathway is also observed.
authors.affiliation: Dipartimento di Chimica Bioorganica e Biofarmacia, Università di Pisa, Via Bonanno 33, 56126 Pisa, Italy.
authors.forename: Valeria
authors.initials: V
authors.lastname: Di Bussolo
authors.forename: Micaela
authors.initials: M
authors.lastname: Caselli
authors.forename: Maria Rosaria
authors.initials: MR
authors.lastname: Romano
authors.forename: Mauro
authors.initials: M
authors.lastname: Pineschi
authors.forename: Paolo
authors.initials: P
authors.lastname: Crotti
mesh_terms: D003847:Deoxyglucose / Q000031:analogs & derivatives* / Q000737:chemistry*; D004852:Epoxy Compounds / Q000138:chemical synthesis*; D005027:Ethylene Oxide / Q000031:analogs & derivatives / Q000138:chemical synthesis*; D008968:Molecular Conformation; D013237:Stereoisomerism; D014753:Vinyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: D004852:Epoxy Compounds; D014753:Vinyl Compounds; C001289:d-glucal; D003847:Deoxyglucose; D005027:Ethylene Oxide