메뉴 건너뛰기




Volumn 39, Issue 12, 2000, Pages 2172-2175

A practical asymmetric synthesis of enantiomerically pure 3-substituted pyroglutamic acids and related compounds

Author keywords

Amino acids; Asymmetric synthesis; Michael additions; Nickel

Indexed keywords

PYROGLUTAMIC ACID; PYROGLUTAMIC ACID DERIVATIVE;

EID: 0034674250     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3773(20000616)39:12<2172::AID-ANIE2172>3.0.CO;2-0     Document Type: Article
Times cited : (85)

References (34)
  • 1
    • 0000545418 scopus 로고
    • 5th ed. (Ed.: M. E. Wolff), John Wiley and Sons, Inc., New York
    • For reviews, see: a) M. Goodman, S. Ro in Burger's Medicinal Chemistry and Drug Discovery, Vol. 1, 5th ed. (Ed.: M. E. Wolff), John Wiley and Sons, Inc., New York, 1995, pp. 803-861;
    • (1995) Burger's Medicinal Chemistry and Drug Discovery , vol.1 , pp. 803-861
    • Goodman, M.1    Ro, S.2
  • 2
    • 0001215147 scopus 로고
    • b) J. Gante, Angew. Chem. 1994, 106, 1780; Angew. Chem. Int. Ed. Engl. 1994, 33, 1699;
    • (1994) Angew. Chem. , vol.106 , pp. 1780
    • Gante, J.1
  • 3
    • 0028038601 scopus 로고
    • b) J. Gante, Angew. Chem. 1994, 106, 1780; Angew. Chem. Int. Ed. Engl. 1994, 33, 1699;
    • (1994) Angew. Chem. Int. Ed. Engl. , vol.33 , pp. 1699
  • 4
    • 0000734566 scopus 로고
    • c) A. Giannis, T. Kolter, Angew. Chem. 1993, 105, 1303; Angew. Chem. Int. Ed. Engl. 1993, 32, 1244;
    • (1993) Angew. Chem. , vol.105 , pp. 1303
    • Giannis, A.1    Kolter, T.2
  • 5
    • 33745502124 scopus 로고
    • c) A. Giannis, T. Kolter, Angew. Chem. 1993, 105, 1303; Angew. Chem. Int. Ed. Engl. 1993, 32, 1244;
    • (1993) Angew. Chem. Int. Ed. Engl. , vol.32 , pp. 1244
  • 12
    • 0037605171 scopus 로고    scopus 로고
    • For a recent review, see: Tetrahedron: Asymmetry 1999, 10, 2245.
    • (1999) Tetrahedron: Asymmetry , vol.10 , pp. 2245
  • 13
  • 22
    • 84981969973 scopus 로고
    • D. Seebach, V. Prelog, Angew. Chem. 1982, 94, 696; Angew. Chem. Int. Ed. Engl. 1982, 21, 654.
    • (1982) Angew. Chem. Int. Ed. Engl. , vol.21 , pp. 654
  • 27
    • 0342895859 scopus 로고    scopus 로고
    • note
    • The corresponding pyroglutamic acids were isolated from the diastereomerically pure nickel(II) complexes (as depicted in Scheme 2) and their spectroscopic and optical properties compared with the literature data (ref. [6]).
  • 28
    • 0343330967 scopus 로고    scopus 로고
    • note
    • Exceptions were cases where α-(R) absolute configuration is a consequence of the Cahn-Ingold-Prelog priority (see ref. [16]) and also some aldol addition reactions where the α-(R) stereochemistry is a result of the rearrangement of the corresponding aldol products forming the β-hydroxy-coordinated complexes. For general patterns of reactivity and stereocontrol properties of complex (S)-1, see ref. [15].
  • 30
    • 0342461734 scopus 로고    scopus 로고
    • (Eds.: I. Ojima, J. R. McCarthy, J. T. Welch), American Chemical Society, Washington, DC, Chap. 2
    • b) V. A. Soloshonok in Biomedical Frontiers of Fluorine Chemistry (Eds.: I. Ojima, J. R. McCarthy, J. T. Welch), American Chemical Society, Washington, DC, 1996, Chap. 2;
    • (1996) Biomedical Frontiers of Fluorine Chemistry
    • Soloshonok, V.A.1
  • 33
    • 84981828672 scopus 로고
    • R. S. Cahn, C. Ingold, V. Prelog, Angew. Chem. 1966, 78, 413; Angew. Chem. Int. Ed. Engl. 1966, 5, 385.
    • (1966) Angew. Chem. Int. Ed. Engl. , vol.5 , pp. 385
  • 34
    • 0342895858 scopus 로고    scopus 로고
    • note
    • For instance: the reactions, recently introduced by us (see ref. [7]), of achiral nickel complexes with the chiral oxazolidin-2-ones, proceeded with high stereochemical outcome but at substantially reduced reaction rates (unpublished results).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.