Asymmetric phase-transfer mediated epoxidation of α,β-unsaturated ketones using catalysts derived from Cinchona alkaloids

Tetrahedron Letters

Volumn 39, Issue 12, 1998, Pages 1599-1602

  Lygo, Barry ^a   Wainwright, Philip G ^a  

^a UNIVERSITY OF SALFORD   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; HYPOCHLORITE SODIUM; KETONE;

ARTICLE; CATALYST; CINCHONA; EPOXIDATION;

EID: 0032546310     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10779-1     Document Type: Article

References (35)

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7. 5. Juliá, S; Masana, J.; Vega, J.C. Angew. Chem. Int. Ed. Engl., 1980, 19, 929; Juliá, S; Guixer, J; Masana, J; Rocas, J; Colonna, S; Annunziata, R; Molinari, H. J. Chem. Soc., Perkin Trans I, 1982, 1317; Colonna, S; Molinari, H; Banfi, S; Juliá, S; Masana, J; Alverez, A. Tetrahedron, 1983, 39, 1635; Banfi, S; Colonna, S; Molinari, H; Juliá, S; Guixer, J. Tetrahedron, 1984, 40, 5207; Bezuidenhoudt, B.C.B; Swanepoel, A; Augustyn, J.A.N; Ferreira, D. Tetrahedron Lett., 1987, 28, 4857; Itsuno, S; Sakakura, M; Ito, K. J. Org. Chem., 1990, 55, 6047; Baures, P.W; Eggleston, D.S; Flisak, J.R; Gombatz, K.J; Lantos, I; Mendelson, W; Remich, J.J. Tetrahedron Lett., 1990, 31, 6501; Flisak, J.R; Gombatz, K.J; Holmes, M.M; Jarmas, A.A; Lantos, I; Mendelson, W.L; Novack, V.J; Remich, J.J; Snyder, L. J. Org. Chem., 1993, 58, 6247; Lasterra-Sánchez, M.E; Roberts, S.M. J. Chem. Soc., Perkin Trans I, 1995, 1467; Kroutil, W; Mayon, P; Lasterra-Sánchez, M.E; Maddrell, S.J; Roberts, S.M; Thornton, S.R; Todd, C.J; Tüter, M. Chem. Commun., 1996, 845, 2495; Lasterra-Sánchez, M.E; Felfer, U; Mayon, P; Roberts, S.M; Thornton, S.R; Todd, C.J. J. Chem. Soc., Perkin Trans I, 1996, 343; Kroutil, W; Lasterra-Sánchez, M.E; Maddrell, S.J; Mayon, P; Morgan, P; Roberts, S.M; Thornton, S.R; Todd, C.J; Tüter, M. J. Chem. Soc., Perkin Trans. I, 1996, 2837; Bentley, P.A; Bergeron, S; Cappi, M.W; Hibbs, D.E; Hursthouse, M.B; Nugent, T.C; Pulido, R; Roberts, S.M; Wu. L.E. Chem. Commun., 1997, 739.
8. 5. Juliá, S; Masana, J.; Vega, J.C. Angew. Chem. Int. Ed. Engl., 1980, 19, 929; Juliá, S; Guixer, J; Masana, J; Rocas, J; Colonna, S; Annunziata, R; Molinari, H. J. Chem. Soc., Perkin Trans I, 1982, 1317; Colonna, S; Molinari, H; Banfi, S; Juliá, S; Masana, J; Alverez, A. Tetrahedron, 1983, 39, 1635; Banfi, S; Colonna, S; Molinari, H; Juliá, S; Guixer, J. Tetrahedron, 1984, 40, 5207; Bezuidenhoudt, B.C.B; Swanepoel, A; Augustyn, J.A.N; Ferreira, D. Tetrahedron Lett., 1987, 28, 4857; Itsuno, S; Sakakura, M; Ito, K. J. Org. Chem., 1990, 55, 6047; Baures, P.W; Eggleston, D.S; Flisak, J.R; Gombatz, K.J; Lantos, I; Mendelson, W; Remich, J.J. Tetrahedron Lett., 1990, 31, 6501; Flisak, J.R; Gombatz, K.J; Holmes, M.M; Jarmas, A.A; Lantos, I; Mendelson, W.L; Novack, V.J; Remich, J.J; Snyder, L. J. Org. Chem., 1993, 58, 6247; Lasterra-Sánchez, M.E; Roberts, S.M. J. Chem. Soc., Perkin Trans I, 1995, 1467; Kroutil, W; Mayon, P; Lasterra-Sánchez, M.E; Maddrell, S.J; Roberts, S.M; Thornton, S.R; Todd, C.J; Tüter, M. Chem. Commun., 1996, 845, 2495; Lasterra-Sánchez, M.E; Felfer, U; Mayon, P; Roberts, S.M; Thornton, S.R; Todd, C.J. J. Chem. Soc., Perkin Trans I, 1996, 343; Kroutil, W; Lasterra-Sánchez, M.E; Maddrell, S.J; Mayon, P; Morgan, P; Roberts, S.M; Thornton, S.R; Todd, C.J; Tüter, M. J. Chem. Soc., Perkin Trans. I, 1996, 2837; Bentley, P.A; Bergeron, S; Cappi, M.W; Hibbs, D.E; Hursthouse, M.B; Nugent, T.C; Pulido, R; Roberts, S.M; Wu. L.E. Chem. Commun., 1997, 739.
9. 5. Juliá, S; Masana, J.; Vega, J.C. Angew. Chem. Int. Ed. Engl., 1980, 19, 929; Juliá, S; Guixer, J; Masana, J; Rocas, J; Colonna, S; Annunziata, R; Molinari, H. J. Chem. Soc., Perkin Trans I, 1982, 1317; Colonna, S; Molinari, H; Banfi, S; Juliá, S; Masana, J; Alverez, A. Tetrahedron, 1983, 39, 1635; Banfi, S; Colonna, S; Molinari, H; Juliá, S; Guixer, J. Tetrahedron, 1984, 40, 5207; Bezuidenhoudt, B.C.B; Swanepoel, A; Augustyn, J.A.N; Ferreira, D. Tetrahedron Lett., 1987, 28, 4857; Itsuno, S; Sakakura, M; Ito, K. J. Org. Chem., 1990, 55, 6047; Baures, P.W; Eggleston, D.S; Flisak, J.R; Gombatz, K.J; Lantos, I; Mendelson, W; Remich, J.J. Tetrahedron Lett., 1990, 31, 6501; Flisak, J.R; Gombatz, K.J; Holmes, M.M; Jarmas, A.A; Lantos, I; Mendelson, W.L; Novack, V.J; Remich, J.J; Snyder, L. J. Org. Chem., 1993, 58, 6247; Lasterra-Sánchez, M.E; Roberts, S.M. J. Chem. Soc., Perkin Trans I, 1995, 1467; Kroutil, W; Mayon, P; Lasterra-Sánchez, M.E; Maddrell, S.J; Roberts, S.M; Thornton, S.R; Todd, C.J; Tüter, M. Chem. Commun., 1996, 845, 2495; Lasterra-Sánchez, M.E; Felfer, U; Mayon, P; Roberts, S.M; Thornton, S.R; Todd, C.J. J. Chem. Soc., Perkin Trans I, 1996, 343; Kroutil, W; Lasterra-Sánchez, M.E; Maddrell, S.J; Mayon, P; Morgan, P; Roberts, S.M; Thornton, S.R; Todd, C.J; Tüter, M. J. Chem. Soc., Perkin Trans. I, 1996, 2837; Bentley, P.A; Bergeron, S; Cappi, M.W; Hibbs, D.E; Hursthouse, M.B; Nugent, T.C; Pulido, R; Roberts, S.M; Wu. L.E. Chem. Commun., 1997, 739.
10. 5. Juliá, S; Masana, J.; Vega, J.C. Angew. Chem. Int. Ed. Engl., 1980, 19, 929; Juliá, S; Guixer, J; Masana, J; Rocas, J; Colonna, S; Annunziata, R; Molinari, H. J. Chem. Soc., Perkin Trans I, 1982, 1317; Colonna, S; Molinari, H; Banfi, S; Juliá, S; Masana, J; Alverez, A. Tetrahedron, 1983, 39, 1635; Banfi, S; Colonna, S; Molinari, H; Juliá, S; Guixer, J. Tetrahedron, 1984, 40, 5207; Bezuidenhoudt, B.C.B; Swanepoel, A; Augustyn, J.A.N; Ferreira, D. Tetrahedron Lett., 1987, 28, 4857; Itsuno, S; Sakakura, M; Ito, K. J. Org. Chem., 1990, 55, 6047; Baures, P.W; Eggleston, D.S; Flisak, J.R; Gombatz, K.J; Lantos, I; Mendelson, W; Remich, J.J. Tetrahedron Lett., 1990, 31, 6501; Flisak, J.R; Gombatz, K.J; Holmes, M.M; Jarmas, A.A; Lantos, I; Mendelson, W.L; Novack, V.J; Remich, J.J; Snyder, L. J. Org. Chem., 1993, 58, 6247; Lasterra-Sánchez, M.E; Roberts, S.M. J. Chem. Soc., Perkin Trans I, 1995, 1467; Kroutil, W; Mayon, P; Lasterra-Sánchez, M.E; Maddrell, S.J; Roberts, S.M; Thornton, S.R; Todd, C.J; Tüter, M. Chem. Commun., 1996, 845, 2495; Lasterra-Sánchez, M.E; Felfer, U; Mayon, P; Roberts, S.M; Thornton, S.R; Todd, C.J. J. Chem. Soc., Perkin Trans I, 1996, 343; Kroutil, W; Lasterra-Sánchez, M.E; Maddrell, S.J; Mayon, P; Morgan, P; Roberts, S.M; Thornton, S.R; Todd, C.J; Tüter, M. J. Chem. Soc., Perkin Trans. I, 1996, 2837; Bentley, P.A; Bergeron, S; Cappi, M.W; Hibbs, D.E; Hursthouse, M.B; Nugent, T.C; Pulido, R; Roberts, S.M; Wu. L.E. Chem. Commun., 1997, 739.
11. 5. Juliá, S; Masana, J.; Vega, J.C. Angew. Chem. Int. Ed. Engl., 1980, 19, 929; Juliá, S; Guixer, J; Masana, J; Rocas, J; Colonna, S; Annunziata, R; Molinari, H. J. Chem. Soc., Perkin Trans I, 1982, 1317; Colonna, S; Molinari, H; Banfi, S; Juliá, S; Masana, J; Alverez, A. Tetrahedron, 1983, 39, 1635; Banfi, S; Colonna, S; Molinari, H; Juliá, S; Guixer, J. Tetrahedron, 1984, 40, 5207; Bezuidenhoudt, B.C.B; Swanepoel, A; Augustyn, J.A.N; Ferreira, D. Tetrahedron Lett., 1987, 28, 4857; Itsuno, S; Sakakura, M; Ito, K. J. Org. Chem., 1990, 55, 6047; Baures, P.W; Eggleston, D.S; Flisak, J.R; Gombatz, K.J; Lantos, I; Mendelson, W; Remich, J.J. Tetrahedron Lett., 1990, 31, 6501; Flisak, J.R; Gombatz, K.J; Holmes, M.M; Jarmas, A.A; Lantos, I; Mendelson, W.L; Novack, V.J; Remich, J.J; Snyder, L. J. Org. Chem., 1993, 58, 6247; Lasterra-Sánchez, M.E; Roberts, S.M. J. Chem. Soc., Perkin Trans I, 1995, 1467; Kroutil, W; Mayon, P; Lasterra-Sánchez, M.E; Maddrell, S.J; Roberts, S.M; Thornton, S.R; Todd, C.J; Tüter, M. Chem. Commun., 1996, 845, 2495; Lasterra-Sánchez, M.E; Felfer, U; Mayon, P; Roberts, S.M; Thornton, S.R; Todd, C.J. J. Chem. Soc., Perkin Trans I, 1996, 343; Kroutil, W; Lasterra-Sánchez, M.E; Maddrell, S.J; Mayon, P; Morgan, P; Roberts, S.M; Thornton, S.R; Todd, C.J; Tüter, M. J. Chem. Soc., Perkin Trans. I, 1996, 2837; Bentley, P.A; Bergeron, S; Cappi, M.W; Hibbs, D.E; Hursthouse, M.B; Nugent, T.C; Pulido, R; Roberts, S.M; Wu. L.E. Chem. Commun., 1997, 739.
12. 5. Juliá, S; Masana, J.; Vega, J.C. Angew. Chem. Int. Ed. Engl., 1980, 19, 929; Juliá, S; Guixer, J; Masana, J; Rocas, J; Colonna, S; Annunziata, R; Molinari, H. J. Chem. Soc., Perkin Trans I, 1982, 1317; Colonna, S; Molinari, H; Banfi, S; Juliá, S; Masana, J; Alverez, A. Tetrahedron, 1983, 39, 1635; Banfi, S; Colonna, S; Molinari, H; Juliá, S; Guixer, J. Tetrahedron, 1984, 40, 5207; Bezuidenhoudt, B.C.B; Swanepoel, A; Augustyn, J.A.N; Ferreira, D. Tetrahedron Lett., 1987, 28, 4857; Itsuno, S; Sakakura, M; Ito, K. J. Org. Chem., 1990, 55, 6047; Baures, P.W; Eggleston, D.S; Flisak, J.R; Gombatz, K.J; Lantos, I; Mendelson, W; Remich, J.J. Tetrahedron Lett., 1990, 31, 6501; Flisak, J.R; Gombatz, K.J; Holmes, M.M; Jarmas, A.A; Lantos, I; Mendelson, W.L; Novack, V.J; Remich, J.J; Snyder, L. J. Org. Chem., 1993, 58, 6247; Lasterra-Sánchez, M.E; Roberts, S.M. J. Chem. Soc., Perkin Trans I, 1995, 1467; Kroutil, W; Mayon, P; Lasterra-Sánchez, M.E; Maddrell, S.J; Roberts, S.M; Thornton, S.R; Todd, C.J; Tüter, M. Chem. Commun., 1996, 845, 2495; Lasterra-Sánchez, M.E; Felfer, U; Mayon, P; Roberts, S.M; Thornton, S.R; Todd, C.J. J. Chem. Soc., Perkin Trans I, 1996, 343; Kroutil, W; Lasterra-Sánchez, M.E; Maddrell, S.J; Mayon, P; Morgan, P; Roberts, S.M; Thornton, S.R; Todd, C.J; Tüter, M. J. Chem. Soc., Perkin Trans. I, 1996, 2837; Bentley, P.A; Bergeron, S; Cappi, M.W; Hibbs, D.E; Hursthouse, M.B; Nugent, T.C; Pulido, R; Roberts, S.M; Wu. L.E. Chem. Commun., 1997, 739.
13. 5. Juliá, S; Masana, J.; Vega, J.C. Angew. Chem. Int. Ed. Engl., 1980, 19, 929; Juliá, S; Guixer, J; Masana, J; Rocas, J; Colonna, S; Annunziata, R; Molinari, H. J. Chem. Soc., Perkin Trans I, 1982, 1317; Colonna, S; Molinari, H; Banfi, S; Juliá, S; Masana, J; Alverez, A. Tetrahedron, 1983, 39, 1635; Banfi, S; Colonna, S; Molinari, H; Juliá, S; Guixer, J. Tetrahedron, 1984, 40, 5207; Bezuidenhoudt, B.C.B; Swanepoel, A; Augustyn, J.A.N; Ferreira, D. Tetrahedron Lett., 1987, 28, 4857; Itsuno, S; Sakakura, M; Ito, K. J. Org. Chem., 1990, 55, 6047; Baures, P.W; Eggleston, D.S; Flisak, J.R; Gombatz, K.J; Lantos, I; Mendelson, W; Remich, J.J. Tetrahedron Lett., 1990, 31, 6501; Flisak, J.R; Gombatz, K.J; Holmes, M.M; Jarmas, A.A; Lantos, I; Mendelson, W.L; Novack, V.J; Remich, J.J; Snyder, L. J. Org. Chem., 1993, 58, 6247; Lasterra-Sánchez, M.E; Roberts, S.M. J. Chem. Soc., Perkin Trans I, 1995, 1467; Kroutil, W; Mayon, P; Lasterra-Sánchez, M.E; Maddrell, S.J; Roberts, S.M; Thornton, S.R; Todd, C.J; Tüter, M. Chem. Commun., 1996, 845, 2495; Lasterra-Sánchez, M.E; Felfer, U; Mayon, P; Roberts, S.M; Thornton, S.R; Todd, C.J. J. Chem. Soc., Perkin Trans I, 1996, 343; Kroutil, W; Lasterra-Sánchez, M.E; Maddrell, S.J; Mayon, P; Morgan, P; Roberts, S.M; Thornton, S.R; Todd, C.J; Tüter, M. J. Chem. Soc., Perkin Trans. I, 1996, 2837; Bentley, P.A; Bergeron, S; Cappi, M.W; Hibbs, D.E; Hursthouse, M.B; Nugent, T.C; Pulido, R; Roberts, S.M; Wu. L.E. Chem. Commun., 1997, 739.
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