10.1016/j.tetasy.2004.08.032
The research describes a method for the synthesis of enantiomerically pure cis- and trans-2-aminocyclohexane-1-carboxylic acids, which are significant due to their potential therapeutic applications and role in forming stable secondary structures in β-peptides. The study utilizes 2-aminobenzamide as a chiral block to assemble quinazolinone, aiming to provide a new synthesis route for all four isomers of 2-aminocyclohexanecarboxylic acid. The process involves chemoselective and diastereoselective hydrogenation of 2,3-dihydro-3-[(S)-α-methylbenzyl]-4-quinazolinone to produce octahydroquinazolinones, which can be epimerized to form their respective stereoisomers. Hydrolysis of these octahydroquinazolinones with HCl yields the desired enantiomerically pure amino acids.