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Issue 3, 1989
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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.

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Article information


J. Chem. Soc., Perkin Trans. 1, 1989, 655-661
Article type
Paper

Stereocontrolled preparation of cyclohexane amino alcohols utilising a modified Mitsunobu reaction

P. G. Sammes and D. Thetford, J. Chem. Soc., Perkin Trans. 1, 1989, 655
DOI: 10.1039/P19890000655

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