Regio- and stereoselectivity of the addition of O-, S-, N-, and C-nucleophiles to the beta vinyl oxirane derived from D-glucal.
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.
Di Bussolo
Valeria
V
Dipartimento di Chimica Bioorganica e Biofarmacia, Università di Pisa, Via Bonanno 33, 56126 Pisa, Italy.
Caselli
Micaela
M
Romano
Maria Rosaria
MR
Pineschi
Mauro
M
Crotti
Paolo
P
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*
D004852:Epoxy Compounds; D014753:Vinyl Compounds; C001289:d-glucal; D003847:Deoxyglucose; D005027:Ethylene Oxide