Asymmetric synthesis of trans-2, 3-piperidinedicarboxylic acid and trans-3, 4-piperidinedicarboxylic acid derivatives

CB Xue, X He, J Roderick, RL Corbett…

Index: Xue, Chu-Biao; He, Xiaohua; Roderick, John; Corbett, Ronald L.; Decicco, Carl P. Journal of Organic Chemistry, 2002 , vol. 67, # 3 p. 865 - 870

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Citation Number: 29

Abstract

Asymmetric syntheses of (2 S, 3 S)-3-(tert-butoxycarbonyl)-2-piperidinecarboxylic acid (1b),(3 R, 4 S)-4-(tert-butoxycarbonyl)-3-piperidinecarboxylic acid (2b), and their corresponding N-Boc and N-Cbz protected analogues 8a, b and 17a, b are described. Enantiomerically pure 1b has been synthesized in five steps starting from l-aspartic acid β- tert-butyl ester. Tribenzylation of the starting material followed by alkylation with allyl ...