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Volumn 37, Issue 22, 1998, Pages 3144-3146

Nickel and palladium catalysis in the stereoselective synthesis of functionalized pyrrolidines: Enantioselective formal synthesis of (+)-α- allokainic acid

Author keywords

Cyclizations; Neurotoxins; Nickel; Palladium; Pyrrolidines

Indexed keywords

ALLOKAINIC ACID; KAINIC ACID; NEUROTOXIN; NICKEL; PALLADIUM; PYRROLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0032484059     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19981204)37:22<3144::AID-ANIE3144>3.0.CO;2-Y     Document Type: Article
Times cited : (48)

References (24)
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    • note
    • a) For an overview of synthetic entries to kainic acid and allokainic acid, see reference [1b];
  • 5
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    • For representative syntheses, see: b) W. Oppolzer, K. Thirring, J. Am. Chem. Soc. 1982, 104, 4978-4979; c) S. Hanessian, S. Ninkovic, J. Org. Chem. 1996, 61, 5418-5424; d) S. Hatakeyama, K. Sugawara, S. Takano, J. Chem. Soc. Chem. Commun. 1993, 125-127; e) C. Agami, M. Cases, F. Couty, J. Org. Chem. 1994, 59, 7937-7940; f) G. A. Kraus, J. O. Nagy, Tetrahedron 1985, 41, 3537-3545; g) H. H. Mooiweer, H. Hiemstra, W. N. Speckamp, Tetrahedron 1991, 47, 3451-3462; h) P. DeShong, D. A. Kell, Tetrahedron Lett. 1986, 27, 3979-3982.
    • (1982) J. Am. Chem. Soc. , vol.104 , pp. 4978-4979
    • Oppolzer, W.1    Thirring, K.2
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    • For representative syntheses, see: b) W. Oppolzer, K. Thirring, J. Am. Chem. Soc. 1982, 104, 4978-4979; c) S. Hanessian, S. Ninkovic, J. Org. Chem. 1996, 61, 5418-5424; d) S. Hatakeyama, K. Sugawara, S. Takano, J. Chem. Soc. Chem. Commun. 1993, 125-127; e) C. Agami, M. Cases, F. Couty, J. Org. Chem. 1994, 59, 7937-7940; f) G. A. Kraus, J. O. Nagy, Tetrahedron 1985, 41, 3537-3545; g) H. H. Mooiweer, H. Hiemstra, W. N. Speckamp, Tetrahedron 1991, 47, 3451-3462; h) P. DeShong, D. A. Kell, Tetrahedron Lett. 1986, 27, 3979-3982.
    • (1996) J. Org. Chem. , vol.61 , pp. 5418-5424
    • Hanessian, S.1    Ninkovic, S.2
  • 7
    • 37049082226 scopus 로고
    • For representative syntheses, see: b) W. Oppolzer, K. Thirring, J. Am. Chem. Soc. 1982, 104, 4978-4979; c) S. Hanessian, S. Ninkovic, J. Org. Chem. 1996, 61, 5418-5424; d) S. Hatakeyama, K. Sugawara, S. Takano, J. Chem. Soc. Chem. Commun. 1993, 125-127; e) C. Agami, M. Cases, F. Couty, J. Org. Chem. 1994, 59, 7937-7940; f) G. A. Kraus, J. O. Nagy, Tetrahedron 1985, 41, 3537-3545; g) H. H. Mooiweer, H. Hiemstra, W. N. Speckamp, Tetrahedron 1991, 47, 3451-3462; h) P. DeShong, D. A. Kell, Tetrahedron Lett. 1986, 27, 3979-3982.
    • (1993) J. Chem. Soc. Chem. Commun. , pp. 125-127
    • Hatakeyama, S.1    Sugawara, K.2    Takano, S.3
  • 8
    • 0028605644 scopus 로고
    • For representative syntheses, see: b) W. Oppolzer, K. Thirring, J. Am. Chem. Soc. 1982, 104, 4978-4979; c) S. Hanessian, S. Ninkovic, J. Org. Chem. 1996, 61, 5418-5424; d) S. Hatakeyama, K. Sugawara, S. Takano, J. Chem. Soc. Chem. Commun. 1993, 125-127; e) C. Agami, M. Cases, F. Couty, J. Org. Chem. 1994, 59, 7937-7940; f) G. A. Kraus, J. O. Nagy, Tetrahedron 1985, 41, 3537-3545; g) H. H. Mooiweer, H. Hiemstra, W. N. Speckamp, Tetrahedron 1991, 47, 3451-3462; h) P. DeShong, D. A. Kell, Tetrahedron Lett. 1986, 27, 3979-3982.
    • (1994) J. Org. Chem. , vol.59 , pp. 7937-7940
    • Agami, C.1    Cases, M.2    Couty, F.3
  • 9
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    • For representative syntheses, see: b) W. Oppolzer, K. Thirring, J. Am. Chem. Soc. 1982, 104, 4978-4979; c) S. Hanessian, S. Ninkovic, J. Org. Chem. 1996, 61, 5418-5424; d) S. Hatakeyama, K. Sugawara, S. Takano, J. Chem. Soc. Chem. Commun. 1993, 125-127; e) C. Agami, M. Cases, F. Couty, J. Org. Chem. 1994, 59, 7937-7940; f) G. A. Kraus, J. O. Nagy, Tetrahedron 1985, 41, 3537-3545; g) H. H. Mooiweer, H. Hiemstra, W. N. Speckamp, Tetrahedron 1991, 47, 3451-3462; h) P. DeShong, D. A. Kell, Tetrahedron Lett. 1986, 27, 3979-3982.
    • (1985) Tetrahedron , vol.41 , pp. 3537-3545
    • Kraus, G.A.1    Nagy, J.O.2
  • 10
    • 0026024156 scopus 로고
    • For representative syntheses, see: b) W. Oppolzer, K. Thirring, J. Am. Chem. Soc. 1982, 104, 4978-4979; c) S. Hanessian, S. Ninkovic, J. Org. Chem. 1996, 61, 5418-5424; d) S. Hatakeyama, K. Sugawara, S. Takano, J. Chem. Soc. Chem. Commun. 1993, 125-127; e) C. Agami, M. Cases, F. Couty, J. Org. Chem. 1994, 59, 7937-7940; f) G. A. Kraus, J. O. Nagy, Tetrahedron 1985, 41, 3537-3545; g) H. H. Mooiweer, H. Hiemstra, W. N. Speckamp, Tetrahedron 1991, 47, 3451-3462; h) P. DeShong, D. A. Kell, Tetrahedron Lett. 1986, 27, 3979-3982.
    • (1991) Tetrahedron , vol.47 , pp. 3451-3462
    • Mooiweer, H.H.1    Hiemstra, H.2    Speckamp, W.N.3
  • 11
    • 0000121278 scopus 로고
    • For representative syntheses, see: b) W. Oppolzer, K. Thirring, J. Am. Chem. Soc. 1982, 104, 4978-4979; c) S. Hanessian, S. Ninkovic, J. Org. Chem. 1996, 61, 5418-5424; d) S. Hatakeyama, K. Sugawara, S. Takano, J. Chem. Soc. Chem. Commun. 1993, 125-127; e) C. Agami, M. Cases, F. Couty, J. Org. Chem. 1994, 59, 7937-7940; f) G. A. Kraus, J. O. Nagy, Tetrahedron 1985, 41, 3537-3545; g) H. H. Mooiweer, H. Hiemstra, W. N. Speckamp, Tetrahedron 1991, 47, 3451-3462; h) P. DeShong, D. A. Kell, Tetrahedron Lett. 1986, 27, 3979-3982.
    • (1986) Tetrahedron Lett. , vol.27 , pp. 3979-3982
    • DeShong, P.1    Kell, D.A.2
  • 14
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    • Reagent 3 was prepared in a fashion analogous to the reported procedure for a phenylalanine-derived reagent: D. A. Evans, W. C. Black, J. Am. Chem. Soc. 1993, 115, 4497-4513.
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 4497-4513
    • Evans, D.A.1    Black, W.C.2
  • 17
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    • note
    • For a conceptually related strategy involving intramolecular protodesilylations, see reference [3d].


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.