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■ Synthesis of 1,3-Linked 1,4-Dihydro-pyridines Containing the L-Tyrosine Residue and the Influence of Their Structures upon the Enantioselective Reduction

Akira Katoh,* Shoichiro Naruse, Junko Ohkanda, and Hiroshi Yamamoto

*Department of Industrial Chemistry, Faculty of Engineering, Seikei University, Musashino-shi, Tokyo 180-8633, Japan

Abstract

Novel 1,3-linked chiral 1,4-dihydropyridines (5a-c) bearing the L-tyrosine residue and the long alkyl chains have been synthesized. The ring size gave a large influence upon the enantioselective reduction of methyl benzoylformate, where 1,12-oxo-2,20-diaza-3-methoxycarbonyl-11-oxa-20,23-dihydro[4,9]metaparacyclophane (5b) showed the highest enantiomer excess (ee, 70%). Further, the 1,3-cyclic structure (5) was demonstrated to be effective on the enantioselective reduction compared to the corresponding acylic one (7), N-(1-propyl-1,4-dihydro-3-pyridylcarbonyl)-L-(O-pentanoyl)tyrosine methyl ester.