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 β-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 TMSN3 or LiN3 are used as azide-based nucleophiles, a 1,2-syn-addition pathway is also observed.
|Autori:||V. DI BUSSOLO; M. CASELLI; M.R. ROMANO; M. PINESCHI; CROTTI P|
|Titolo:||Regio- and Stereoselectivity of the Addition of O-, S-, N-, and C-Nucleophiles to the beta Vinyl Oxirane Derived from D-Glucal|
|Anno del prodotto:||2004|
|Digital Object Identifier (DOI):||10.1021/jo048981b|
|Appare nelle tipologie:||1.1 Articolo in rivista|