Facile Regio- and Diastereoselective Syntheses of Hydroxylated2-Aminocyclohexanecarboxylic Acids

By means of total regio- and diastereoselective functionalizations of cis- and trans-2-amino-4-cyclohexenecarboxylic acid derivatives 1, 9, 12 and 16, isomers of 2-amino-4-hydroxycyclohexanecarboxylic acid 8 and 11, and 2-amino-5-hydroxycyclohexanecarboxylic acid 15 and 19 were prepared in good yields, via 1,3-oxazine or γ-lactone intermediates. The enantiomers of 8 and 15 were also prepared by the same pathway, resulting in products with ee > 99 %. The structures, stereochemistry and relative configurations of the synthesized compounds were proved by NMR, using some key vicinal couplings and characteristic NOEs. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)