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.

Regio- and Stereoselectivity of the Addition of O-, S-, N-, and C-Nucleophiles to the beta Vinyl Oxirane Derived from D-Glucal

DI BUSSOLO, VALERIA;PINESCHI, MAURO;CROTTI, PAOLO
2004

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 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.
DI BUSSOLO, Valeria; M., Caselli; M. R., Romano; Pineschi, Mauro; Crotti, Paolo
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11568/181615
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