Stereoselective synthesis of hydroxylated β-aminocyclohexanecarboxylic acids

A simple synthetic approach has been developed for the regio- and diastereoselective synthesis of hydroxylated 2-aminocyclohexanecarboxylic acid stereoisomers from 1,4-cyclohexadiene by the reductive opening of appropriate epoxide intermediates derived from the corresponding bicyclic beta-lactams. This method has been extended to the synthesis of these hydroxylated p-amino acids in enantiomerically pure form. (C) 2008 Elsevier Ltd. All rights reserved.