Tetrahedron: Asymmetry

Steric constraints against [3, 3]-sigmatropic rearrangement of allylic azides. A convenient approach to β-l-4-aminopent-2-enoglyceropyranosides

C Fava, R Galeazzi, G Mobbili, M Orena

Index: Fava, Cristiana; Galeazzi, Roberta; Mobbili, Giovanna; Orena, Mario Tetrahedron Asymmetry, 2001 , vol. 12, # 19 p. 2731 - 2741

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Citation Number: 18

Abstract

Starting from alkyl α-d-4-O-methanesulphonylpent-2-enoglyceropyranosides 13a–c, nucleophilic substitution carried out with polymer-supported azide ion led to regioisomeric mixtures of the azides 14a–c and 15a–c. An analogous result, due to a [3, 3]-sigmatropic rearrangement, was observed starting from methyl α-d-hex-2-enoerythropyranoside derivatives 6a and 6b. On the contrary, starting from alkyl β-d-4-O-methanesulphonylpent- ...