Synlett

A Chiral Imidazoline Nitrone; A Cycloaddition Route to Imidazoisoxazoles and Pyrroloimidazoles

RCF Jones, JN Martin, P Smith

Index: Jones, Raymond C. F.; Martin, Jason N.; Smith, Paul Synlett, 2000 , # 7 p. 967 - 970

Full Text: HTML

Citation Number: 14

Abstract

Abstract: A chiral imidazolinium 3-oxide has been prepared, that undergoes diastereoselective dipolar cycloaddition with alkenes to afford imidazo [1, 2-b] isoxazoles; a suitable cycloadduct undergoes NO cleavage and recyclisation leading to a pyrrolo [1, 2-a] imidazole and thence potentially to pyrrolidines. Key words: imidazoisoxazoles, nitrones, cycloadditions, heterocycles, bicyclic compounds