title: New stereoselective beta-C-glycosidation by uncatalyzed 1,4-addition of organolithium reagents to a glycal-derived vinyl oxirane.
abstract: [reaction: see text] Epoxide 4 is generated in situ from d-glucal-derived hydroxy mesylate 3. Reaction of epoxide 4 with a series of alkyl- and aryllithium reagents affords 2,3-unsaturated beta-C-glycosides with excellent 1,4-regioselectivity and complete stereoselectivity for the beta-glycoside. Other organometallic reagents demonstrate more complex behavior in their reactions with epoxide 4.
authors.affiliation: Dipartimento di Chimica Bioorganica e Biofarmacia, Università di Pisa, Via Bonanno 33, I-56126 Pisa, Italy.
authors.forename: Valeria
authors.initials: V
authors.lastname: Di Bussolo
authors.forename: Micaela
authors.initials: M
authors.lastname: Caselli
authors.forename: Mauro
authors.initials: M
authors.lastname: Pineschi
authors.forename: Paolo
authors.initials: P
authors.lastname: Crotti
mesh_terms: D005027:Ethylene Oxide / Q000737:chemistry*; D005960:Glucosides / Q000138:chemical synthesis*; D006031:Glycosylation; D008094:Lithium / Q000737:chemistry*; D009942:Organometallic Compounds / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D005960:Glucosides; D009942:Organometallic Compounds; D008094:Lithium; D005027:Ethylene Oxide