Asymmetric syntheses of trans-3, 4-disubstituted 2-piperidinones and piperidines

LT Liu, PC Hong, HL Huang, SF Chen, CLJ Wang…

Index: Liu, Lee Tai; Hong, Pao-Chiung; Huang, Hsiang-Ling; Chen, Shyh-Fong; Wang, Chia-Lin Jeff; Wen, Yuh-Sheng Tetrahedron Asymmetry, 2001 , vol. 12, # 3 p. 419 - 426

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Citation Number: 55

Abstract

A convenient and practical method for the preparation of chiral 4-aryl-2-piperidinone from 3- arylglutaric anhydride and (S)-methylbenzylamine is described. Acylation or alkylation at the α-carbon of the chiral 4-aryl-2-piperidinone product afforded chiral trans-3, 4-disubstituted 2- piperidinone derivatives and reduction of the chiral 2-piperidinones with lithium aluminum hydride provided the corresponding enantiomerically pure trans-3, 4-disubstituted ...