Regio- and Stereoselectivity of the Addition of <i>O</i>-, <i>S</i>-, <i>N</i>-, and <i>C</i>-Nucleophiles to the β Vinyl Oxirane Derived from <scp>d</scp>-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.