DESIGN AND SYNTHESIS OF HAPTENS FOR APPLICATION TO THE PREPARATION OFCHIRAL 1,4-DIHYDROPYRIDINES

Lipase-catalyzed enzymatic hydrolysis of dimethyl esters of 1,4-dihydr opyridines to the monoester, which is an important intermediate for th e synthesis of optically active 1,4-dihydropyridines, does not proceed directly. This paper describes the design and synthesis of novel hapt ens having a phosphonate group containing the requisite oxyanionic cha racter to mimic the tetrahedral intermediate of hydrolysis, and the ap plication of these compounds for generating antibodies with catalytic ability for the enantioselective partial hydrolysis of the dicarboxyli c dimethyl ester (1) of a 1,1-dihydropyridine derivative to generate t he monocarboxylic acid (2).