Stereoselective nucleophilic substitution of 6-methoxy-1-methoxycarbonylpipecolate: enantioselective synthesis of (+)-sedamine from L-lysine

K Irie, K Aoe, T Tanaka, S Saito

Index: Irie, K.; Aoe, K.; Tanaka, T.; Saito, S. Journal of the Chemical Society, Chemical Communications, 1985 , # 10 p. 633 - 635

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Citation Number: 28

Abstract

Amidoalkylation 6-methoxy-I -methoxycarbonylpipecolate (4) with several nucleophiles gave the 2,6-cis 6-substituted pipecolates, stereoselectively. ... We recently reported that electrochemical oxidation of the Na,N&-bis(methoxycarbony1)-L-lysine ester (1) gave the 6-aminopipecolate derivative (2) , which could be converted into (2s)-pipecolic acid (3), sustaining the chirality of the starting material. 1 We have now found that the condensations of the 6- ...