Enzymatic resolution of 2-substituted tetrahydroquinolines. Convenient approaches to tricyclic quinoxalinediones as potent NMDA-glycine antagonists

S Katayama, N Ae, R Nagata

Index: Katayama, Seiji; Ae, Nobuyuki; Nagata, Ryu Tetrahedron Asymmetry, 1998 , vol. 9, # 24 p. 4295 - 4299

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Citation Number: 45

Abstract

Two approaches leading to the enantiomerically pure tricyclic quinoxalinedione class of NMDA-glycine antagonists using enzymatic resolutions are described. An intermediate, racemic methyl 1, 2, 3, 4-tetrahydroquinoline-2-carboxylate 3, was resolved to (S)-3 in 97% ee and 47% yield (E= 67) using α-chymotrypsin. In an improved method, hydrolysis of another intermediate, racemic methyl 1, 2, 3, 4-tetrahydroquinoline-2-acetate 4, with ...