Stereocontrolled preparation of cyclohexane amino alcohols utilising a modified Mitsunobu reaction

Abstract

A method for the introduction of amino groups into aliphatic systems is described. Cyclohex-2-enol reacts with aromatic diacylamines under Mitsunobu reaction conditions to give either N-alkylated or O-alkylated products in a controlled, predictable manner. The product cyclohexenes, with N-bromosuccinimide, give either 1,2- or 1,3-neighbouring group participation leading to 1,2,3-trisubstituted cyclohexanes. The adducts may be used to give a range of 1,2- and 1,3-amino alcohols in a stereocontrolled process.