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

页码：3515 / 3525

页数：11

共 38 条

[1]

Agami C, 1998, EUR J ORG CHEM, V1998, P2461

[2] 1,3-DIPOLAR CYCLOADDITION AS THE KEY REACTION IN THE SYNTHESIS OF POTENT RENIN INHIBITORS [J].

BENZ, G ;

HENNING, R ;

STASCH, JP .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1991, 30 (12) :1702-1704

[3]

Dömling A, 1998, COMB CHEM HIGH T SCR, V1, P1

[4] Pseudo-prolines as a molecular hinge: Reversible induction of cis amide bonds into peptide backbones [J].

Dumy, P ;

Keller, M ;

Ryan, DE ;

Rohwedder, B ;

Wohr, T ;

Mutter, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (05) :918-925

[5] RECENT DEVELOPMENTS IN THE STEREOSELECTIVE SYNTHESIS OF ALPHA-AMINO-ACIDS [J].

DUTHALER, RO .

TETRAHEDRON, 1994, 50 (06) :1539-1650

[6]

DUTTA A S, 1988, Drugs of the Future, V13, P43

[7]

Eliel E.L., 1994, Stereochemistry of Organic Compounds

[8] TIN TETRACHLORIDE-INDUCED PI-CYCLIZATIONS OF GLYCINE CATION EQUIVALENTS TO SUBSTITUTED PIPECOLIC ACID-DERIVATIVES [J].

ESCH, PM ;

BOSKA, IM ;

HIEMSTRA, H ;

DEBOER, RF ;

SPECKAMP, WN .

TETRAHEDRON, 1991, 47 (24) :4039-4062

[9] CONFORMATIONALLY CONSTRAINED NONPEPTIDE BETA-TURN MIMETICS OF ENKEPHALIN [J].

GARDNER, B ;

NAKANISHI, H ;

KAHN, M .

TETRAHEDRON, 1993, 49 (17) :3433-3448

[10] DESIGN, SYNTHESIS, AND X-RAY CRYSTALLOGRAPHIC ANALYSIS OF 2 NOVEL SPIROLACTAM SYSTEMS AS BETA-TURN MIMICS [J].

GENIN, MJ ;

GLEASON, WB ;

JOHNSON, RL .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (04) :860-866

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