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Issue 23, 1999
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Synthesis of novel pipecolic acid derivatives: a multicomponent approach from 3,4,5,6-tetrahydropyridines

Abstract

A simple approach to several derivatives of pipecolic acid is via a multicomponent reaction starting from cyclic imines 2, which are synthesized on a large scale and with different substitution patterns. The protected amino acids 3 are formed in high yields. In cases where chiral imines are used the target compounds are obtained with remarkable diastereoselectivity. Bisamides 3 serve as versatile precursors for the preparation of a wide range of amino acid derivatives. Different methods of hydrolysis of 3 lead to the free pipecolic acids or its derivatives. Employment of methanol or ethanethiol as a nucleophile in the acid-mediated conversion of enamides 3 results in N-acylated amino acid esters 5. Furthermore a method for the resolution of the obtained racemic α-amino acids via diastereomeric salt formation is described.

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Article type: Paper
DOI: 10.1039/A905119H
J. Chem. Soc., Perkin Trans. 1, 1999, 3515-3525

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    Synthesis of novel pipecolic acid derivatives: a multicomponent approach from 3,4,5,6-tetrahydropyridines

    W. Maison, A. Lützen, M. Kosten, I. Schlemminger, O. Westerhoff and J. Martens, J. Chem. Soc., Perkin Trans. 1, 1999, 3515
    DOI: 10.1039/A905119H

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