메뉴 건너뛰기




Volumn 82, Issue 7, 1999, Pages 981-1004

Asymmetric phase-transfer catalysis by quaternary ammonium ions derived from Cinchona-alkaloid analogs containing 1,1'-binaphthalene moieties

Author keywords

[No Author keywords available]

Indexed keywords

1,1' BINAPHTHALENE DERIVATIVE; CINCHONA ALKALOID; QUINUCLIDINEMETHANOL; UNCLASSIFIED DRUG;

EID: 0032770267     PISSN: 0018019X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1522-2675(19990707)82:7<981::AID-HLCA981>3.0.CO;2-V     Document Type: Article
Times cited : (19)

References (102)
  • 6
    • 0001776104 scopus 로고    scopus 로고
    • Ed. Y. Sasson and R. Neumann, Blackie Academic & Professional, London
    • T. Shioiri in 'Handbook of Phase Transfer Catalysis', Ed. Y. Sasson and R. Neumann, Blackie Academic & Professional, London, 1997, pp. 462-479.
    • (1997) Handbook of Phase Transfer Catalysis , pp. 462-479
    • Shioiri, T.1
  • 12
    • 84985534954 scopus 로고
    • b) A. Bhattacharya, U.-H. Dolling, E. J. J. Grabowski, S. Karady, K. M. Ryan, L. M. Weinstock, Angew. Chem. 1986, 98, 442; ibid., Int. Ed. 1986, 25, 476;
    • (1986) Angew. Chem., Int. Ed. , vol.25 , pp. 476
  • 15
    • 33845185214 scopus 로고
    • M. J. O'Donnell, J. Am. Chem. Soc. 1989, 111, 2353; K. B. Lipkowitz, M. W. Cavanaugh, B. Baker, M. J. O'Donnell, J. Org. Chem. 1991, 56, 5181; M. J. O'Donnell, S. Wu, Tetrahedron: Asymmetry 1992, 3, 591; M. J. O'Donnell, S. Wu, J. C. Huffman, Tetrahedron 1994, 50, 4507; M. J. O'Donnell, F. Delgado, C. Hostettler, R. Schwesinger, Tetrahedron Lett. 1998, 39, 8775.
    • (1989) J. Am. Chem. Soc. , vol.111 , pp. 2353
    • O'Donnell, M.J.1
  • 16
    • 0000344872 scopus 로고
    • M. J. O'Donnell, J. Am. Chem. Soc. 1989, 111, 2353; K. B. Lipkowitz, M. W. Cavanaugh, B. Baker, M. J. O'Donnell, J. Org. Chem. 1991, 56, 5181; M. J. O'Donnell, S. Wu, Tetrahedron: Asymmetry 1992, 3, 591; M. J. O'Donnell, S. Wu, J. C. Huffman, Tetrahedron 1994, 50, 4507; M. J. O'Donnell, F. Delgado, C. Hostettler, R. Schwesinger, Tetrahedron Lett. 1998, 39, 8775.
    • (1991) J. Org. Chem. , vol.56 , pp. 5181
    • Lipkowitz, K.B.1    Cavanaugh, M.W.2    Baker, B.3    O'Donnell, M.J.4
  • 17
    • 0026652090 scopus 로고
    • M. J. O'Donnell, J. Am. Chem. Soc. 1989, 111, 2353; K. B. Lipkowitz, M. W. Cavanaugh, B. Baker, M. J. O'Donnell, J. Org. Chem. 1991, 56, 5181; M. J. O'Donnell, S. Wu, Tetrahedron: Asymmetry 1992, 3, 591; M. J. O'Donnell, S. Wu, J. C. Huffman, Tetrahedron 1994, 50, 4507; M. J. O'Donnell, F. Delgado, C. Hostettler, R. Schwesinger, Tetrahedron Lett. 1998, 39, 8775.
    • (1992) Tetrahedron: Asymmetry , vol.3 , pp. 591
    • O'Donnell, M.J.1    Wu, S.2
  • 18
    • 0028300898 scopus 로고
    • M. J. O'Donnell, J. Am. Chem. Soc. 1989, 111, 2353; K. B. Lipkowitz, M. W. Cavanaugh, B. Baker, M. J. O'Donnell, J. Org. Chem. 1991, 56, 5181; M. J. O'Donnell, S. Wu, Tetrahedron: Asymmetry 1992, 3, 591; M. J. O'Donnell, S. Wu, J. C. Huffman, Tetrahedron 1994, 50, 4507; M. J. O'Donnell, F. Delgado, C. Hostettler, R. Schwesinger, Tetrahedron Lett. 1998, 39, 8775.
    • (1994) Tetrahedron , vol.50 , pp. 4507
    • O'Donnell, M.J.1    Wu, S.2    Huffman, J.C.3
  • 19
    • 0032569863 scopus 로고    scopus 로고
    • M. J. O'Donnell, J. Am. Chem. Soc. 1989, 111, 2353; K. B. Lipkowitz, M. W. Cavanaugh, B. Baker, M. J. O'Donnell, J. Org. Chem. 1991, 56, 5181; M. J. O'Donnell, S. Wu, Tetrahedron: Asymmetry 1992, 3, 591; M. J. O'Donnell, S. Wu, J. C. Huffman, Tetrahedron 1994, 50, 4507; M. J. O'Donnell, F. Delgado, C. Hostettler, R. Schwesinger, Tetrahedron Lett. 1998, 39, 8775.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 8775
    • O'Donnell, M.J.1    Delgado, F.2    Hostettler, C.3    Schwesinger, R.4
  • 20
    • 0000234063 scopus 로고    scopus 로고
    • E. J. Corey, F. Xu, M. C Noe, J. Am. Chem. Soc. 1997, 119, 12414; E. J. Corey, M. C. Noe, F. Xu, Tetrahedron Lett. 1998, 39, 5347; see also: E. J. Corey, Y. Bo, J. Busch-Petersen, J. Am. Chem. Soc. 1998, 120, 13000.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 12414
    • Corey, E.J.1    Xu, F.2    Noe, M.C.3
  • 21
    • 0032560703 scopus 로고    scopus 로고
    • E. J. Corey, F. Xu, M. C Noe, J. Am. Chem. Soc. 1997, 119, 12414; E. J. Corey, M. C. Noe, F. Xu, Tetrahedron Lett. 1998, 39, 5347; see also: E. J. Corey, Y. Bo, J. Busch-Petersen, J. Am. Chem. Soc. 1998, 120, 13000.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 5347
    • Corey, E.J.1    Noe, M.C.2    Xu, F.3
  • 22
    • 0032539189 scopus 로고    scopus 로고
    • E. J. Corey, F. Xu, M. C Noe, J. Am. Chem. Soc. 1997, 119, 12414; E. J. Corey, M. C. Noe, F. Xu, Tetrahedron Lett. 1998, 39, 5347; see also: E. J. Corey, Y. Bo, J. Busch-Petersen, J. Am. Chem. Soc. 1998, 120, 13000.
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 13000
    • Corey, E.J.1    Bo, Y.2    Busch-Petersen, J.3
  • 24
    • 0033547985 scopus 로고    scopus 로고
    • B. Lygo, J. Crosby, J. A. Peterson, Tetrahedron Lett. 1999, 40, 1385; B. Lygo, ibid. 1999, 40, 1389.
    • (1999) Tetrahedron Lett. , vol.40 , pp. 1389
    • Lygo, B.1
  • 26
    • 0025788671 scopus 로고
    • A. Ando, T. Miura, T. Tatematsu, T. Shioiri, Tetrahedron Lett. 1993, 34, 1507; C. M. Gasparski, M. J. Miller, Tetrahedron 1991, 47, 5367.
    • (1991) Tetrahedron , vol.47 , pp. 5367
    • Gasparski, C.M.1    Miller, M.J.2
  • 27
    • 0000867232 scopus 로고
    • R. S. E. Conn, A. V. Lovell, S. Karady, L. M. Weinstock, J. Org. Chem. 1986, 51, 4710; A. Loupy, J. Sansoulet, A. Zaparucha, C. Merienne, Tetrahedron Lett. 1989, 30, 333; S. Colonna, H. Hiemstra, H. Wynberg, J. Chem. Soc., Chem. Commun. 1978, 238.
    • (1986) J. Org. Chem. , vol.51 , pp. 4710
    • Conn, R.S.E.1    Lovell, A.V.2    Karady, S.3    Weinstock, L.M.4
  • 28
    • 0000680405 scopus 로고
    • R. S. E. Conn, A. V. Lovell, S. Karady, L. M. Weinstock, J. Org. Chem. 1986, 51, 4710; A. Loupy, J. Sansoulet, A. Zaparucha, C. Merienne, Tetrahedron Lett. 1989, 30, 333; S. Colonna, H. Hiemstra, H. Wynberg, J. Chem. Soc., Chem. Commun. 1978, 238.
    • (1989) Tetrahedron Lett. , vol.30 , pp. 333
    • Loupy, A.1    Sansoulet, J.2    Zaparucha, A.3    Merienne, C.4
  • 29
    • 10844270846 scopus 로고
    • R. S. E. Conn, A. V. Lovell, S. Karady, L. M. Weinstock, J. Org. Chem. 1986, 51, 4710; A. Loupy, J. Sansoulet, A. Zaparucha, C. Merienne, Tetrahedron Lett. 1989, 30, 333; S. Colonna, H. Hiemstra, H. Wynberg, J. Chem. Soc., Chem. Commun. 1978, 238.
    • (1978) J. Chem. Soc., Chem. Commun. , pp. 238
    • Colonna, S.1    Hiemstra, H.2    Wynberg, H.3
  • 33
    • 85050272509 scopus 로고
    • Eds. E. L. Eliel, S. H. Wilen, N. L. Allinger, Wiley, New York
    • d) H. Wynberg in Topics in Stereochemistry', Vol. 16, Eds. E. L. Eliel, S. H. Wilen, N. L. Allinger, Wiley, New York, 1986, pp. 87-129.
    • (1986) Topics in Stereochemistry , vol.16 , pp. 87-129
    • Wynberg, H.1
  • 35
    • 0344450348 scopus 로고
    • S. Colonna, R. Fornasier, Synthesis 1975, 531; S. Juliá, A. Ginebreda, J. Guixer, J. Masana, A. Tomás, S. Colonna, J. Chem. Soc., Perkin Trans. 1 1981, 574.
    • (1975) Synthesis , vol.531
    • Colonna, S.1    Fornasier, R.2
  • 38
    • 0000067960 scopus 로고
    • Ed. I. Ojima, VCH, New York
    • R. A. Johnson, K. B. Sharpless in 'Catalytic Asymmetric Synthesis', Ed. I. Ojima, VCH, New York, 1993, pp. 227-272; H. C. Kolb, M. S. VanNieuwenhze, K. B. Sharpless, Chem. Rev. 1994, 94, 2483.
    • (1993) Catalytic Asymmetric Synthesis , pp. 227-272
    • Johnson, R.A.1    Sharpless, K.B.2
  • 39
    • 4444276636 scopus 로고
    • R. A. Johnson, K. B. Sharpless in 'Catalytic Asymmetric Synthesis', Ed. I. Ojima, VCH, New York, 1993, pp. 227-272; H. C. Kolb, M. S. VanNieuwenhze, K. B. Sharpless, Chem. Rev. 1994, 94, 2483.
    • (1994) Chem. Rev. , vol.94 , pp. 2483
    • Kolb, H.C.1    VanNieuwenhze, M.S.2    Sharpless, K.B.3
  • 40
    • 0003467190 scopus 로고
    • Ed. E. L. Eliel, University of Notre Dame Press, Notre Dame
    • S. H. Wilen, 'Tables of Resolving Agents and Optical Resolutions', Ed. E. L. Eliel, University of Notre Dame Press, Notre Dame, 1972; J. Jacques, A. Collet, S. H. Wilen in 'Enantiomers, Racemates and Resolution', Wiley, New York, 1981.
    • (1972) Tables of Resolving Agents and Optical Resolutions
    • Wilen, S.H.1
  • 43
    • 0345313245 scopus 로고
    • C. Rosini, L. Franzini, A. Raffaelli, P. Salvadori, Synthesis 1992, 503; L. Pu, Chem. Rev. 1998, 2405; H. Brunner and W. Zettlmeier, 'Handbook of Enantioselective Catalysis with Transition Metal Compounds', VCH, Weinheim, 1993, Vols. 1 and 2; R. Noyori, 'Asymmetric Catalysis' Wiley, New York, 1994.
    • (1992) Synthesis , vol.503
    • Rosini, C.1    Franzini, L.2    Raffaelli, A.3    Salvadori, P.4
  • 44
    • 0000718373 scopus 로고    scopus 로고
    • C. Rosini, L. Franzini, A. Raffaelli, P. Salvadori, Synthesis 1992, 503; L. Pu, Chem. Rev. 1998, 2405; H. Brunner and W. Zettlmeier, 'Handbook of Enantioselective Catalysis with Transition Metal Compounds', VCH, Weinheim, 1993, Vols. 1 and 2; R. Noyori, 'Asymmetric Catalysis' Wiley, New York, 1994.
    • (1998) Chem. Rev. , pp. 2405
    • Pu, L.1
  • 46
    • 0003615223 scopus 로고
    • Wiley, New York
    • C. Rosini, L. Franzini, A. Raffaelli, P. Salvadori, Synthesis 1992, 503; L. Pu, Chem. Rev. 1998, 2405; H. Brunner and W. Zettlmeier, 'Handbook of Enantioselective Catalysis with Transition Metal Compounds', VCH, Weinheim, 1993, Vols. 1 and 2; R. Noyori, 'Asymmetric Catalysis' Wiley, New York, 1994.
    • (1994) Asymmetric Catalysis
    • Noyori, R.1
  • 48
    • 33947094923 scopus 로고
    • G. W. Gokel, 'Crown Ethers and Cryptands, Monographs in Supramolecular Chemistry', Ed. J. F. Stoddart, The Royal Society of Chemistry, Cambridge, 1991; D. J. Cram, J. M. Cram, Acc. Chem. Res. 1978, 11, 8.
    • (1978) Acc. Chem. Res. , vol.11 , pp. 8
    • Cram, D.J.1    Cram, J.M.2
  • 49
    • 0000329554 scopus 로고
    • S. Anderson, U. Neidlein, V. Gramlich, F. Diederich, Angew. Chem. 1995, 107, 1722; ibid., Int. Ed 1995, 34, 1596; U. Neidlein, F. Diederich, J. Chem. Soc., Chem. Commun. 1996, 1493; A. Bähr, A. S. Droz, M. Püntener, U. Neidlein, S. Anderson, P. Seiler, F. Diederich, Helv. Chim. Acta 1998, 81, 1931.
    • (1995) Angew. Chem. , vol.107 , pp. 1722
    • Anderson, S.1    Neidlein, U.2    Gramlich, V.3    Diederich, F.4
  • 50
    • 0342553400 scopus 로고
    • S. Anderson, U. Neidlein, V. Gramlich, F. Diederich, Angew. Chem. 1995, 107, 1722; ibid., Int. Ed 1995, 34, 1596; U. Neidlein, F. Diederich, J. Chem. Soc., Chem. Commun. 1996, 1493; A. Bähr, A. S. Droz, M. Püntener, U. Neidlein, S. Anderson, P. Seiler, F. Diederich, Helv. Chim. Acta 1998, 81, 1931.
    • (1995) Angew. Chem., Int. Ed , vol.34 , pp. 1596
  • 51
    • 0002670428 scopus 로고    scopus 로고
    • S. Anderson, U. Neidlein, V. Gramlich, F. Diederich, Angew. Chem. 1995, 107, 1722; ibid., Int. Ed 1995, 34, 1596; U. Neidlein, F. Diederich, J. Chem. Soc., Chem. Commun. 1996, 1493; A. Bähr, A. S. Droz, M. Püntener, U. Neidlein, S. Anderson, P. Seiler, F. Diederich, Helv. Chim. Acta 1998, 81, 1931.
    • (1996) J. Chem. Soc., Chem. Commun. , pp. 1493
    • Neidlein, U.1    Diederich, F.2
  • 55
    • 33845184812 scopus 로고
    • E. Martinborough, T. Mordasini Denti, P. P. Castro, T. B. Wyman, C. B. Knobler, F. Diederich, Helv. Chim. Acta 1995, 78, 1037; P. Lustenberger, E. Martinborough, T. Mordasini Denti, F. Diederich, J. Chem. Soc., Perkin Trans. 2 1998, 747; P. P. Castro, T. M. Georgiadis, F. Diederich, J. Org. Chem. 1989, 54, 5835.
    • (1989) J. Org. Chem. , vol.54 , pp. 5835
    • Castro, P.P.1    Georgiadis, T.M.2    Diederich, F.3
  • 56
    • 0001431569 scopus 로고    scopus 로고
    • H.-Y. Li, T. Nehira, M. Hagiwara, N. Harada, J. Org. Chem. 1997, 62, 7222; T. Hattori, K. Sakurai, N. Koike, S. Miyano, H. Goto, F. Ishiya, N. Harada, J. Am. Chem. Soc. 1998, 120, 9086.
    • (1997) J. Org. Chem. , vol.62 , pp. 7222
    • Li, H.-Y.1    Nehira, T.2    Hagiwara, M.3    Harada, N.4
  • 59
    • 0032473509 scopus 로고    scopus 로고
    • E. J. Corey, A. Guzman-Perez, Angew. Chem. 1998, 110, 402; ibid., Int. Ed. 1998, 37, 388.
    • (1998) Angew. Chem., Int. Ed. , vol.37 , pp. 388
  • 65
    • 0011403831 scopus 로고    scopus 로고
    • M. Schneider, A. Baiker,Cat. Rev.-Sci. Eng. 1995, 37, 515; N. Hüsing, U. Schubert, Angew. Chem. 1998, 110, 22; ibid., Int. Ed. 1998, 37, 22; R. J. P. Corriu, D. Leclercq, Angew. Chem. 1996, 108, 1524; ibid., Int. Ed. 1996, 35, 1420.
    • (1995) Cat. Rev.-Sci. Eng. , vol.37 , pp. 515
    • Schneider, M.1    Baiker, A.2
  • 66
    • 0031906650 scopus 로고    scopus 로고
    • M. Schneider, A. Baiker,Cat. Rev.-Sci. Eng. 1995, 37, 515; N. Hüsing, U. Schubert, Angew. Chem. 1998, 110, 22; ibid., Int. Ed. 1998, 37, 22; R. J. P. Corriu, D. Leclercq, Angew. Chem. 1996, 108, 1524; ibid., Int. Ed. 1996, 35, 1420.
    • (1998) Angew. Chem. , vol.110 , pp. 22
    • Hüsing, N.1    Schubert, U.2
  • 67
    • 0011403831 scopus 로고    scopus 로고
    • M. Schneider, A. Baiker,Cat. Rev.-Sci. Eng. 1995, 37, 515; N. Hüsing, U. Schubert, Angew. Chem. 1998, 110, 22; ibid., Int. Ed. 1998, 37, 22; R. J. P. Corriu, D. Leclercq, Angew. Chem. 1996, 108, 1524; ibid., Int. Ed. 1996, 35, 1420.
    • (1998) Angew. Chem., Int. Ed. , vol.37 , pp. 22
  • 68
    • 0011403831 scopus 로고    scopus 로고
    • M. Schneider, A. Baiker,Cat. Rev.-Sci. Eng. 1995, 37, 515; N. Hüsing, U. Schubert, Angew. Chem. 1998, 110, 22; ibid., Int. Ed. 1998, 37, 22; R. J. P. Corriu, D. Leclercq, Angew. Chem. 1996, 108, 1524; ibid., Int. Ed. 1996, 35, 1420.
    • (1996) Angew. Chem. , vol.108 , pp. 1524
    • Corriu, R.J.P.1    Leclercq, D.2
  • 69
    • 0029759266 scopus 로고    scopus 로고
    • M. Schneider, A. Baiker,Cat. Rev.-Sci. Eng. 1995, 37, 515; N. Hüsing, U. Schubert, Angew. Chem. 1998, 110, 22; ibid., Int. Ed. 1998, 37, 22; R. J. P. Corriu, D. Leclercq, Angew. Chem. 1996, 108, 1524; ibid., Int. Ed. 1996, 35, 1420.
    • (1996) Angew. Chem., Int. Ed. , vol.35 , pp. 1420
  • 94
    • 0024343737 scopus 로고
    • G. D. H. Dijkstra, R. M. Kellogg, H. Wynberg, J. S. Svendsen, I. Marko, K. B. Sharpless, J. Am. Chem. Soc. 1989, 111, 8069; G. D. H. Dijkstra, R. M. Kellogg, H. Wynberg, J. Org. Chem. 1990, 55, 6121; F. I. Carroll, P. Abraham, K. Gaetano, S. W. Mascarella, R. A. Wohl, J. Lind, K. Petzoldt, J. Chem. Soc., Perkin Trans. 1 1991, 3017; U. Berg, M. Aune, O. Matsson, Tetrahedron Lett. 1995, 36, 2137.
    • (1989) J. Am. Chem. Soc. , vol.111 , pp. 8069
    • Dijkstra, G.D.H.1    Kellogg, R.M.2    Wynberg, H.3    Svendsen, J.S.4    Marko, I.5    Sharpless, K.B.6
  • 95
    • 0025673823 scopus 로고
    • G. D. H. Dijkstra, R. M. Kellogg, H. Wynberg, J. S. Svendsen, I. Marko, K. B. Sharpless, J. Am. Chem. Soc. 1989, 111, 8069; G. D. H. Dijkstra, R. M. Kellogg, H. Wynberg, J. Org. Chem. 1990, 55, 6121; F. I. Carroll, P. Abraham, K. Gaetano, S. W. Mascarella, R. A. Wohl, J. Lind, K. Petzoldt, J. Chem. Soc., Perkin Trans. 1 1991, 3017; U. Berg, M. Aune, O. Matsson, Tetrahedron Lett. 1995, 36, 2137.
    • (1990) J. Org. Chem. , vol.55 , pp. 6121
    • Dijkstra, G.D.H.1    Kellogg, R.M.2    Wynberg, H.3
  • 97
    • 0028959424 scopus 로고
    • G. D. H. Dijkstra, R. M. Kellogg, H. Wynberg, J. S. Svendsen, I. Marko, K. B. Sharpless, J. Am. Chem. Soc. 1989, 111, 8069; G. D. H. Dijkstra, R. M. Kellogg, H. Wynberg, J. Org. Chem. 1990, 55, 6121; F. I. Carroll, P. Abraham, K. Gaetano, S. W. Mascarella, R. A. Wohl, J. Lind, K. Petzoldt, J. Chem. Soc., Perkin Trans. 1 1991, 3017; U. Berg, M. Aune, O. Matsson, Tetrahedron Lett. 1995, 36, 2137.
    • (1995) Tetrahedron Lett. , vol.36 , pp. 2137
    • Berg, U.1    Aune, M.2    Matsson, O.3
  • 99
    • 0026620007 scopus 로고
    • S. J. Weiner, P. A. Kollman, D. A. Case, U. C. Singh, C. Ghio, G. Alagona, S. Profeta, Jr., P. Weiner, J. Am. Chem. Soc. 1984, 106, 765; D. Q. McDonald, W. C. Still, Tetrahedron Lett. 1992, 33, 7743.
    • (1992) Tetrahedron Lett. , vol.33 , pp. 7743
    • McDonald, D.Q.1    Still, W.C.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.