261917-70-8Relevant articles and documents
Synthesis of novel pipecolic acid derivatives: A multicomponent approach from 3, 4, 5, 6-tetrahydropyridines
Maison, Wolfgang,Liitzcn, Arne,Kosten, Marc,Schlcmminger, Imre,Westerhoff, Ole,Martens, Juergen
, p. 3515 - 3525 (2007/10/03)
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 W-acylated amino acid esters 5. Furthermore a method for the resolution of the obtained racemic a-amino acids via diastereomeric salt formation is described. The Royal Society of Chemistry 1999.