Asymmetric synthesis of (2R,5R)-2,5-diaminohexan-1,6-dioic acid

Tetrahedron

Volumn 54, Issue 35, 1998, Pages 10379-10388

  Bull, Steven D ^a   Chernega, Alexander N ^a   Davies, Stephen G ^a   Moss, William O ^b   Parkin, Richard M ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

^b ASTRAZENECA   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

1,2 BIS[3,6 DIHYDRO 2,5 DIMETHOXY 3 ISOPROPYLPYRAZIN 6 YL]ETHANE; 2,5 DIAMINOHEXAN 1,6 DIOIC ACID; DIAMINOPIMELIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CRYSTAL STRUCTURE; PRIORITY JOURNAL; STEREOISOMERISM; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0032572864     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00492-X     Document Type: Article

References (37)

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26. 12. a) Homochiral (S,S)-2,5-diaminohexan-1,6-dioic acid has been prepared previously by resolution using chiral HPLC according to the method of J. B. Ducep, B. Heintzelmann, K. Jund, B. Lesur, M. Schleimer and P. R. Zimmermann, Tetrahedron: Asymmetry, 1997, 8, 327;
27. b) or via papain catalysed stereoselective amide bond formation between a racemic mixture of (SS)-, (SR)-and (AA)-N,N'-dibenzoyl-2,5-diaminohexanedioic acids and aniline according to the method of K. Toi and Y. Izumi, Nippon Kagaku Zasshi, 1960, 81, 652.
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33. 17. meso-DAD 25 is easily prepared via cycloaddition between cyclohexadiene and dibenzoyldiazine using Diels-Alder methodology developed by Y. Arakawa, T. Goto, K. Kawase and S. Yoshifuji, Chem. Pharm. Bull., 1995, 43, 535.
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