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

被引:22
作者
Maison, W [1 ]
Lützen, A [1 ]
Kosten, M [1 ]
Schlemminger, I [1 ]
Westerhoff, O [1 ]
Martens, J [1 ]
机构
[1] Carl von Ossietzky Univ Oldenburg, Dept Organ Chem, D-26111 Oldenburg, Germany
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1999年 / 23期
关键词
D O I
10.1039/a905119h
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
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 alpha-amino acids via diastereomeric salt formation is described.
引用
收藏
页码:3515 / 3525
页数:11
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