PREPARATION OF NOVEL HETEROCYCLIC AMINO-ACIDS FROM N-(ARYLMETHYLENE)DEHYDROALANINE METHYL-ESTERS

被引：22

作者：

WULFF, G

KLINKEN, HT

机构：

[1] Institute of Organic Chemistry and Macromolecular Chemistry, Heinrich-Heine University Düsseldorf, 4000 Düsseldorf 1

来源：

TETRAHEDRON | 1992年 / 48卷 / 29期

关键词：

ALPHA; ALPHA'-DIAMINODICARBOXYLIC ACIDS; 3-AMINO-PIPERIDINE-3,6-DICARBOXYLIC ACIDS; 2,6-DIAZABICYCLO[3.2.1]OCTANE-1,5-DICARBOXYLIC ACIDS; NONPROTEINOGENIC AMINO ACIDS;

D O I：

10.1016/S0040-4020(01)89847-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

N-(Arylmethylene)dehydroalanine methyl esters undergo a stereoregulated dimerization reaction to produce heterocyclic alpha,alpha'-diaminodicarboxylic acid derivatives. Further transformation yields stable hydrochlorides of free alpha,alpha'-diaminodicarboxylic acids which represent either substituted 3-amino-piperidine-3,6-dicarboxylic acids or substituted 2,6-diazabicyclo[3.2.1]octane-1,5-dicarboxylic acids. These compounds represent new types of cyclic and bicyclic amino acids.

引用

页码：5985 / 5990

页数：6

共 19 条

[1]

[Anonymous], 1985, HYDROGENATION METHOD

[2]

BARRETT GC, 1985, CHEM BIOCH AMINO ACI

[3]

Bohnke H., 1984, ANGEW CHEM, V96, P362

[4]

CODY W L, 1987, Acta Universitatis Palackianae Olomucensis Facultatis Medicae, V116, P495

[5]

JAGNOW G, 1985, BIOTECHNOLOGIE

[6] TWO-DIMENSIONAL NMR-SPECTROSCOPY - BACKGROUND AND OVERVIEW OF THE EXPERIMENTS [J].

KESSLER, H ;

GEHRKE, M ;

GRIESINGER, C .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1988, 27 (04) :490-536

[7]

KESSLER H, 1988, ANGEW CHEM, V100, P507

[8] ON AMINO-ACIDS AND PEPTIDES .28. DEHYDRO AMINO-ACIDS .14. SCHIFF-BASES OF DEHYDRO AMINO-ACIDS FROM 2-ARYL-4-THIAZOLIDINECARBOXYLIC ACIDS - 1ST SYNTHESIS OF AN N-ARYLIDENE-DEHYDROALANINE ESTER [J].

OHLER, E ;

SCHMIDT, U .

CHEMISCHE BERICHTE-RECUEIL, 1979, 112 (01) :107-115

[9]

SEEBACH D, 1989, LIEBIGS ANN CHEM, P1215

[10] AN IMPROVED SYNTHESIS OF HOMOPROLINE AND DERIVATIVES [J].

SHUMAN, RT ;

ORNSTEIN, PL ;

PASCHAL, JW ;

GESELLCHEN, PD .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (02) :738-741

← 1 2 →