Issue 9, 2004

An efficient synthesis of 2-amino alcohols by silica gel catalysed opening of epoxide rings by amines

Abstract

Silica gel (60–120 mesh) efficiently catalyses the opening of epoxide rings by amines at rt under solvent-free conditions providing an easy method for the synthesis of 2-amino alcohols. Aromatic and aliphatic amines react with cyclohexene oxide with exclusive formation of the trans-2-aryl/alkylaminocyclohexanols in high yields. A complementary regioselectivity is exhibited by aromatic and aliphatic amines during the reaction with styrene oxide. The epoxide ring of non-styrenoidal unsymmetrical alkene oxide undergoes selective nucleophilic attack at the sterically less hindered carbon by aniline.

Graphical abstract: An efficient synthesis of 2-amino alcohols by silica gel catalysed opening of epoxide rings by amines

Article information

Article type
Paper
Submitted
13 Jan 2004
Accepted
09 Mar 2004
First published
29 Mar 2004

Org. Biomol. Chem., 2004,2, 1277-1280

An efficient synthesis of 2-amino alcohols by silica gel catalysed opening of epoxide rings by amines

A. K. Chakraborti, S. Rudrawar and A. Kondaskar, Org. Biomol. Chem., 2004, 2, 1277 DOI: 10.1039/B400588K

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