Phase-transfer catalysed asymmetric epoxidation of enones using N- anthracenylmethyl-substituted cinchona alkaloids

Tetrahedron

Volumn 55, Issue 20, 1999, Pages 6289-6300

  Lygo, B ^a   Wainwright, P G ^a  

^a UNIVERSITY OF SALFORD   (United Kingdom)

Author keywords

Asymmetric phase transfer catalysis; Cinchona alkaloids; Enones; Epoxidation; Quaternary ammonium salts

Indexed keywords

ALKENE DERIVATIVE; ANTHRACENE DERIVATIVE; CINCHONA ALKALOID; HYPOCHLORITE SODIUM; KETONE; QUATERNARY AMMONIUM DERIVATIVE;

ARTICLE; CATALYSIS; EPOXIDATION; PHASE TRANSITION; PRIORITY JOURNAL; REACTION TIME; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033553370     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00205-7     Document Type: Article

References (54)

1. 1. Fruh, T. Agro. Food Indust. Hi-Tech., 1996, 7, 31; Ebrahim, S; Wills, M. Tetrahedron Asymm., 1997, 8, 3163.
2. 1. Fruh, T. Agro. Food Indust. Hi-Tech., 1996, 7, 31; Ebrahim, S; Wills, M. Tetrahedron Asymm., 1997, 8, 3163.
3. 2. Good enantioselectivities have also been achieved using non-catalytic systems involving molecular oxygen in the presence of diethylzinc/chiral amino alcohols, see: Enders, D; Zhu, J; Raabe, G. Angew. Chem. Int. Ed. Engl., 1996, 35, 1725; Enders, D; Zhu, J. Kramps, L. Ann., 1997, 1101.
4. 2. Good enantioselectivities have also been achieved using non-catalytic systems involving molecular oxygen in the presence of diethylzinc/chiral amino alcohols, see: Enders, D; Zhu, J; Raabe, G. Angew. Chem. Int. Ed. Engl., 1996, 35, 1725; Enders, D; Zhu, J. Kramps, L. Ann., 1997, 1101.
5. 3. (a) Juliá, S; Masana, J.; Vega, J.C. Angew. Chem. Int. Ed. Engl., 1980, 19, 929; (b) Juliá, S; Guixer, J; Masana, J; Rocas, J; Colonna, S; Annunziata, R; Molinari, H. J. Chem. Soc., Perkin Trans I, 1982, 1317; (c) Colonna, S; Molinari, H; Banfi, S; Juliá, S; Masana, J; Alverez, A. Tetrahedron, 1983, 39, 1635; (d) Banfi, S; Colonna, S; Molinari, H; Juliá, S; Guixer, J. Tetrahedron, 1984, 40, 5207; (e) Bezuidenhoudt, B.C.B; Swanepoel, A; Augustyn, J.A.N; Ferreira, D. Tetrahedron Lett., 1987, 28, 4857; (f) Itsuno, S; Sakakura, M; Ito, K. J. Org. Chem., 1990, 55, 6047; (g) Baures, P.W; Eggleston, D.S; Flisak, J.R; Gombatz, K.J; Lantos, I; Mendelson, W; Remich, J.J. Tetrahedron Lett., 1990, 31, 6501; (h) 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; (i) Lasterra-Sánchez, M.E; Roberts, S.M. J. Chem. Soc., Perkin Trans I, 1995, 1467; (j) 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; (k) 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; (l) 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; (m) 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; (n) Allen, J.V; Cappi, M.W; Kary, P.D; Roberts, S.M; Williamson, N.M; Wu, L.E. J. Chem. Soc., Perkin Trans. I, 1997, 3297; (o) Adger, B.M; Barkley, J.V; Bergeron, S; Cappi, M.W; Flowerdew, B.E; Jackson, M.P; McCague, R; Nugent, T.C; Roberts, S.M. J. Chem. Soc., Perkin Trans. I, 1997, 3501; (p) Cappi, M.W; Chen, W.-P; Flood, R.W; Liao, Y.-W; Roberts, S.M; Skidmore, J; Smith, J. A; Williamson, N.M. Chem. Commun., 1998, 1159.
6. 3. (a) Juliá, S; Masana, J.; Vega, J.C. Angew. Chem. Int. Ed. Engl., 1980, 19, 929; (b) Juliá, S; Guixer, J; Masana, J; Rocas, J; Colonna, S; Annunziata, R; Molinari, H. J. Chem. Soc., Perkin Trans I, 1982, 1317; (c) Colonna, S; Molinari, H; Banfi, S; Juliá, S; Masana, J; Alverez, A. Tetrahedron, 1983, 39, 1635; (d) Banfi, S; Colonna, S; Molinari, H; Juliá, S; Guixer, J. Tetrahedron, 1984, 40, 5207; (e) Bezuidenhoudt, B.C.B; Swanepoel, A; Augustyn, J.A.N; Ferreira, D. Tetrahedron Lett., 1987, 28, 4857; (f) Itsuno, S; Sakakura, M; Ito, K. J. Org. Chem., 1990, 55, 6047; (g) Baures, P.W; Eggleston, D.S; Flisak, J.R; Gombatz, K.J; Lantos, I; Mendelson, W; Remich, J.J. Tetrahedron Lett., 1990, 31, 6501; (h) 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; (i) Lasterra-Sánchez, M.E; Roberts, S.M. J. Chem. Soc., Perkin Trans I, 1995, 1467; (j) 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; (k) 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; (l) 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; (m) 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; (n) Allen, J.V; Cappi, M.W; Kary, P.D; Roberts, S.M; Williamson, N.M; Wu, L.E. J. Chem. Soc., Perkin Trans. I, 1997, 3297; (o) Adger, B.M; Barkley, J.V; Bergeron, S; Cappi, M.W; Flowerdew, B.E; Jackson, M.P; McCague, R; Nugent, T.C; Roberts, S.M. J. Chem. Soc., Perkin Trans. I, 1997, 3501; (p) Cappi, M.W; Chen, W.-P; Flood, R.W; Liao, Y.-W; Roberts, S.M; Skidmore, J; Smith, J. A; Williamson, N.M. Chem. Commun., 1998, 1159.
7. 3. (a) Juliá, S; Masana, J.; Vega, J.C. Angew. Chem. Int. Ed. Engl., 1980, 19, 929; (b) Juliá, S; Guixer, J; Masana, J; Rocas, J; Colonna, S; Annunziata, R; Molinari, H. J. Chem. Soc., Perkin Trans I, 1982, 1317; (c) Colonna, S; Molinari, H; Banfi, S; Juliá, S; Masana, J; Alverez, A. Tetrahedron, 1983, 39, 1635; (d) Banfi, S; Colonna, S; Molinari, H; Juliá, S; Guixer, J. Tetrahedron, 1984, 40, 5207; (e) Bezuidenhoudt, B.C.B; Swanepoel, A; Augustyn, J.A.N; Ferreira, D. Tetrahedron Lett., 1987, 28, 4857; (f) Itsuno, S; Sakakura, M; Ito, K. J. Org. Chem., 1990, 55, 6047; (g) Baures, P.W; Eggleston, D.S; Flisak, J.R; Gombatz, K.J; Lantos, I; Mendelson, W; Remich, J.J. Tetrahedron Lett., 1990, 31, 6501; (h) 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; (i) Lasterra-Sánchez, M.E; Roberts, S.M. J. Chem. Soc., Perkin Trans I, 1995, 1467; (j) 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; (k) 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; (l) 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; (m) 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; (n) Allen, J.V; Cappi, M.W; Kary, P.D; Roberts, S.M; Williamson, N.M; Wu, L.E. J. Chem. Soc., Perkin Trans. I, 1997, 3297; (o) Adger, B.M; Barkley, J.V; Bergeron, S; Cappi, M.W; Flowerdew, B.E; Jackson, M.P; McCague, R; Nugent, T.C; Roberts, S.M. J. Chem. Soc., Perkin Trans. I, 1997, 3501; (p) Cappi, M.W; Chen, W.-P; Flood, R.W; Liao, Y.-W; Roberts, S.M; Skidmore, J; Smith, J. A; Williamson, N.M. Chem. Commun., 1998, 1159.
8. 3. (a) Juliá, S; Masana, J.; Vega, J.C. Angew. Chem. Int. Ed. Engl., 1980, 19, 929; (b) Juliá, S; Guixer, J; Masana, J; Rocas, J; Colonna, S; Annunziata, R; Molinari, H. J. Chem. Soc., Perkin Trans I, 1982, 1317; (c) Colonna, S; Molinari, H; Banfi, S; Juliá, S; Masana, J; Alverez, A. Tetrahedron, 1983, 39, 1635; (d) Banfi, S; Colonna, S; Molinari, H; Juliá, S; Guixer, J. Tetrahedron, 1984, 40, 5207; (e) Bezuidenhoudt, B.C.B; Swanepoel, A; Augustyn, J.A.N; Ferreira, D. Tetrahedron Lett., 1987, 28, 4857; (f) Itsuno, S; Sakakura, M; Ito, K. J. Org. Chem., 1990, 55, 6047; (g) Baures, P.W; Eggleston, D.S; Flisak, J.R; Gombatz, K.J; Lantos, I; Mendelson, W; Remich, J.J. Tetrahedron Lett., 1990, 31, 6501; (h) 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; (i) Lasterra-Sánchez, M.E; Roberts, S.M. J. Chem. Soc., Perkin Trans I, 1995, 1467; (j) 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; (k) 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; (l) 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; (m) 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; (n) Allen, J.V; Cappi, M.W; Kary, P.D; Roberts, S.M; Williamson, N.M; Wu, L.E. J. Chem. Soc., Perkin Trans. I, 1997, 3297; (o) Adger, B.M; Barkley, J.V; Bergeron, S; Cappi, M.W; Flowerdew, B.E; Jackson, M.P; McCague, R; Nugent, T.C; Roberts, S.M. J. Chem. Soc., Perkin Trans. I, 1997, 3501; (p) Cappi, M.W; Chen, W.-P; Flood, R.W; Liao, Y.-W; Roberts, S.M; Skidmore, J; Smith, J. A; Williamson, N.M. Chem. Commun., 1998, 1159.
9. 3. (a) Juliá, S; Masana, J.; Vega, J.C. Angew. Chem. Int. Ed. Engl., 1980, 19, 929; (b) Juliá, S; Guixer, J; Masana, J; Rocas, J; Colonna, S; Annunziata, R; Molinari, H. J. Chem. Soc., Perkin Trans I, 1982, 1317; (c) Colonna, S; Molinari, H; Banfi, S; Juliá, S; Masana, J; Alverez, A. Tetrahedron, 1983, 39, 1635; (d) Banfi, S; Colonna, S; Molinari, H; Juliá, S; Guixer, J. Tetrahedron, 1984, 40, 5207; (e) Bezuidenhoudt, B.C.B; Swanepoel, A; Augustyn, J.A.N; Ferreira, D. Tetrahedron Lett., 1987, 28, 4857; (f) Itsuno, S; Sakakura, M; Ito, K. J. Org. Chem., 1990, 55, 6047; (g) Baures, P.W; Eggleston, D.S; Flisak, J.R; Gombatz, K.J; Lantos, I; Mendelson, W; Remich, J.J. Tetrahedron Lett., 1990, 31, 6501; (h) 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; (i) Lasterra-Sánchez, M.E; Roberts, S.M. J. Chem. Soc., Perkin Trans I, 1995, 1467; (j) 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; (k) 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; (l) 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; (m) 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; (n) Allen, J.V; Cappi, M.W; Kary, P.D; Roberts, S.M; Williamson, N.M; Wu, L.E. J. Chem. Soc., Perkin Trans. I, 1997, 3297; (o) Adger, B.M; Barkley, J.V; Bergeron, S; Cappi, M.W; Flowerdew, B.E; Jackson, M.P; McCague, R; Nugent, T.C; Roberts, S.M. J. Chem. Soc., Perkin Trans. I, 1997, 3501; (p) Cappi, M.W; Chen, W.-P; Flood, R.W; Liao, Y.-W; Roberts, S.M; Skidmore, J; Smith, J. A; Williamson, N.M. Chem. Commun., 1998, 1159.
10. 3. (a) Juliá, S; Masana, J.; Vega, J.C. Angew. Chem. Int. Ed. Engl., 1980, 19, 929; (b) Juliá, S; Guixer, J; Masana, J; Rocas, J; Colonna, S; Annunziata, R; Molinari, H. J. Chem. Soc., Perkin Trans I, 1982, 1317; (c) Colonna, S; Molinari, H; Banfi, S; Juliá, S; Masana, J; Alverez, A. Tetrahedron, 1983, 39, 1635; (d) Banfi, S; Colonna, S; Molinari, H; Juliá, S; Guixer, J. Tetrahedron, 1984, 40, 5207; (e) Bezuidenhoudt, B.C.B; Swanepoel, A; Augustyn, J.A.N; Ferreira, D. Tetrahedron Lett., 1987, 28, 4857; (f) Itsuno, S; Sakakura, M; Ito, K. J. Org. Chem., 1990, 55, 6047; (g) Baures, P.W; Eggleston, D.S; Flisak, J.R; Gombatz, K.J; Lantos, I; Mendelson, W; Remich, J.J. Tetrahedron Lett., 1990, 31, 6501; (h) 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; (i) Lasterra-Sánchez, M.E; Roberts, S.M. J. Chem. Soc., Perkin Trans I, 1995, 1467; (j) 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; (k) 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; (l) 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; (m) 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; (n) Allen, J.V; Cappi, M.W; Kary, P.D; Roberts, S.M; Williamson, N.M; Wu, L.E. J. Chem. Soc., Perkin Trans. I, 1997, 3297; (o) Adger, B.M; Barkley, J.V; Bergeron, S; Cappi, M.W; Flowerdew, B.E; Jackson, M.P; McCague, R; Nugent, T.C; Roberts, S.M. J. Chem. Soc., Perkin Trans. I, 1997, 3501; (p) Cappi, M.W; Chen, W.-P; Flood, R.W; Liao, Y.-W; Roberts, S.M; Skidmore, J; Smith, J. A; Williamson, N.M. Chem. Commun., 1998, 1159.
11. 3. (a) Juliá, S; Masana, J.; Vega, J.C. Angew. Chem. Int. Ed. Engl., 1980, 19, 929; (b) Juliá, S; Guixer, J; Masana, J; Rocas, J; Colonna, S; Annunziata, R; Molinari, H. J. Chem. Soc., Perkin Trans I, 1982, 1317; (c) Colonna, S; Molinari, H; Banfi, S; Juliá, S; Masana, J; Alverez, A. Tetrahedron, 1983, 39, 1635; (d) Banfi, S; Colonna, S; Molinari, H; Juliá, S; Guixer, J. Tetrahedron, 1984, 40, 5207; (e) Bezuidenhoudt, B.C.B; Swanepoel, A; Augustyn, J.A.N; Ferreira, D. Tetrahedron Lett., 1987, 28, 4857; (f) Itsuno, S; Sakakura, M; Ito, K. J. Org. Chem., 1990, 55, 6047; (g) Baures, P.W; Eggleston, D.S; Flisak, J.R; Gombatz, K.J; Lantos, I; Mendelson, W; Remich, J.J. Tetrahedron Lett., 1990, 31, 6501; (h) 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; (i) Lasterra-Sánchez, M.E; Roberts, S.M. J. Chem. Soc., Perkin Trans I, 1995, 1467; (j) 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; (k) 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; (l) 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; (m) 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; (n) Allen, J.V; Cappi, M.W; Kary, P.D; Roberts, S.M; Williamson, N.M; Wu, L.E. J. Chem. Soc., Perkin Trans. I, 1997, 3297; (o) Adger, B.M; Barkley, J.V; Bergeron, S; Cappi, M.W; Flowerdew, B.E; Jackson, M.P; McCague, R; Nugent, T.C; Roberts, S.M. J. Chem. Soc., Perkin Trans. I, 1997, 3501; (p) Cappi, M.W; Chen, W.-P; Flood, R.W; Liao, Y.-W; Roberts, S.M; Skidmore, J; Smith, J. A; Williamson, N.M. Chem. Commun., 1998, 1159.
12. 3. (a) Juliá, S; Masana, J.; Vega, J.C. Angew. Chem. Int. Ed. Engl., 1980, 19, 929; (b) Juliá, S; Guixer, J; Masana, J; Rocas, J; Colonna, S; Annunziata, R; Molinari, H. J. Chem. Soc., Perkin Trans I, 1982, 1317; (c) Colonna, S; Molinari, H; Banfi, S; Juliá, S; Masana, J; Alverez, A. Tetrahedron, 1983, 39, 1635; (d) Banfi, S; Colonna, S; Molinari, H; Juliá, S; Guixer, J. Tetrahedron, 1984, 40, 5207; (e) Bezuidenhoudt, B.C.B; Swanepoel, A; Augustyn, J.A.N; Ferreira, D. Tetrahedron Lett., 1987, 28, 4857; (f) Itsuno, S; Sakakura, M; Ito, K. J. Org. Chem., 1990, 55, 6047; (g) Baures, P.W; Eggleston, D.S; Flisak, J.R; Gombatz, K.J; Lantos, I; Mendelson, W; Remich, J.J. Tetrahedron Lett., 1990, 31, 6501; (h) 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; (i) Lasterra-Sánchez, M.E; Roberts, S.M. J. Chem. Soc., Perkin Trans I, 1995, 1467; (j) 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; (k) 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; (l) 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; (m) 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; (n) Allen, J.V; Cappi, M.W; Kary, P.D; Roberts, S.M; Williamson, N.M; Wu, L.E. J. Chem. Soc., Perkin Trans. I, 1997, 3297; (o) Adger, B.M; Barkley, J.V; Bergeron, S; Cappi, M.W; Flowerdew, B.E; Jackson, M.P; McCague, R; Nugent, T.C; Roberts, S.M. J. Chem. Soc., Perkin Trans. I, 1997, 3501; (p) Cappi, M.W; Chen, W.-P; Flood, R.W; Liao, Y.-W; Roberts, S.M; Skidmore, J; Smith, J. A; Williamson, N.M. Chem. Commun., 1998, 1159.
13. 3. (a) Juliá, S; Masana, J.; Vega, J.C. Angew. Chem. Int. Ed. Engl., 1980, 19, 929; (b) Juliá, S; Guixer, J; Masana, J; Rocas, J; Colonna, S; Annunziata, R; Molinari, H. J. Chem. Soc., Perkin Trans I, 1982, 1317; (c) Colonna, S; Molinari, H; Banfi, S; Juliá, S; Masana, J; Alverez, A. Tetrahedron, 1983, 39, 1635; (d) Banfi, S; Colonna, S; Molinari, H; Juliá, S; Guixer, J. Tetrahedron, 1984, 40, 5207; (e) Bezuidenhoudt, B.C.B; Swanepoel, A; Augustyn, J.A.N; Ferreira, D. Tetrahedron Lett., 1987, 28, 4857; (f) Itsuno, S; Sakakura, M; Ito, K. J. Org. Chem., 1990, 55, 6047; (g) Baures, P.W; Eggleston, D.S; Flisak, J.R; Gombatz, K.J; Lantos, I; Mendelson, W; Remich, J.J. Tetrahedron Lett., 1990, 31, 6501; (h) 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; (i) Lasterra-Sánchez, M.E; Roberts, S.M. J. Chem. Soc., Perkin Trans I, 1995, 1467; (j) 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; (k) 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; (l) 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; (m) 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; (n) Allen, J.V; Cappi, M.W; Kary, P.D; Roberts, S.M; Williamson, N.M; Wu, L.E. J. Chem. Soc., Perkin Trans. I, 1997, 3297; (o) Adger, B.M; Barkley, J.V; Bergeron, S; Cappi, M.W; Flowerdew, B.E; Jackson, M.P; McCague, R; Nugent, T.C; Roberts, S.M. J. Chem. Soc., Perkin Trans. I, 1997, 3501; (p) Cappi, M.W; Chen, W.-P; Flood, R.W; Liao, Y.-W; Roberts, S.M; Skidmore, J; Smith, J. A; Williamson, N.M. Chem. Commun., 1998, 1159.
14. 3. (a) Juliá, S; Masana, J.; Vega, J.C. Angew. Chem. Int. Ed. Engl., 1980, 19, 929; (b) Juliá, S; Guixer, J; Masana, J; Rocas, J; Colonna, S; Annunziata, R; Molinari, H. J. Chem. Soc., Perkin Trans I, 1982, 1317; (c) Colonna, S; Molinari, H; Banfi, S; Juliá, S; Masana, J; Alverez, A. Tetrahedron, 1983, 39, 1635; (d) Banfi, S; Colonna, S; Molinari, H; Juliá, S; Guixer, J. Tetrahedron, 1984, 40, 5207; (e) Bezuidenhoudt, B.C.B; Swanepoel, A; Augustyn, J.A.N; Ferreira, D. Tetrahedron Lett., 1987, 28, 4857; (f) Itsuno, S; Sakakura, M; Ito, K. J. Org. Chem., 1990, 55, 6047; (g) Baures, P.W; Eggleston, D.S; Flisak, J.R; Gombatz, K.J; Lantos, I; Mendelson, W; Remich, J.J. Tetrahedron Lett., 1990, 31, 6501; (h) 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; (i) Lasterra-Sánchez, M.E; Roberts, S.M. J. Chem. Soc., Perkin Trans I, 1995, 1467; (j) 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; (k) 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; (l) 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; (m) 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; (n) Allen, J.V; Cappi, M.W; Kary, P.D; Roberts, S.M; Williamson, N.M; Wu, L.E. J. Chem. Soc., Perkin Trans. I, 1997, 3297; (o) Adger, B.M; Barkley, J.V; Bergeron, S; Cappi, M.W; Flowerdew, B.E; Jackson, M.P; McCague, R; Nugent, T.C; Roberts, S.M. J. Chem. Soc., Perkin Trans. I, 1997, 3501; (p) Cappi, M.W; Chen, W.-P; Flood, R.W; Liao, Y.-W; Roberts, S.M; Skidmore, J; Smith, J. A; Williamson, N.M. Chem. Commun., 1998, 1159.
15. 3. (a) Juliá, S; Masana, J.; Vega, J.C. Angew. Chem. Int. Ed. Engl., 1980, 19, 929; (b) Juliá, S; Guixer, J; Masana, J; Rocas, J; Colonna, S; Annunziata, R; Molinari, H. J. Chem. Soc., Perkin Trans I, 1982, 1317; (c) Colonna, S; Molinari, H; Banfi, S; Juliá, S; Masana, J; Alverez, A. Tetrahedron, 1983, 39, 1635; (d) Banfi, S; Colonna, S; Molinari, H; Juliá, S; Guixer, J. Tetrahedron, 1984, 40, 5207; (e) Bezuidenhoudt, B.C.B; Swanepoel, A; Augustyn, J.A.N; Ferreira, D. Tetrahedron Lett., 1987, 28, 4857; (f) Itsuno, S; Sakakura, M; Ito, K. J. Org. Chem., 1990, 55, 6047; (g) Baures, P.W; Eggleston, D.S; Flisak, J.R; Gombatz, K.J; Lantos, I; Mendelson, W; Remich, J.J. Tetrahedron Lett., 1990, 31, 6501; (h) 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; (i) Lasterra-Sánchez, M.E; Roberts, S.M. J. Chem. Soc., Perkin Trans I, 1995, 1467; (j) 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; (k) 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; (l) 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; (m) 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; (n) Allen, J.V; Cappi, M.W; Kary, P.D; Roberts, S.M; Williamson, N.M; Wu, L.E. J. Chem. Soc., Perkin Trans. I, 1997, 3297; (o) Adger, B.M; Barkley, J.V; Bergeron, S; Cappi, M.W; Flowerdew, B.E; Jackson, M.P; McCague, R; Nugent, T.C; Roberts, S.M. J. Chem. Soc., Perkin Trans. I, 1997, 3501; (p) Cappi, M.W; Chen, W.-P; Flood, R.W; Liao, Y.-W; Roberts, S.M; Skidmore, J; Smith, J. A; Williamson, N.M. Chem. Commun., 1998, 1159.
16. 3. (a) Juliá, S; Masana, J.; Vega, J.C. Angew. Chem. Int. Ed. Engl., 1980, 19, 929; (b) Juliá, S; Guixer, J; Masana, J; Rocas, J; Colonna, S; Annunziata, R; Molinari, H. J. Chem. Soc., Perkin Trans I, 1982, 1317; (c) Colonna, S; Molinari, H; Banfi, S; Juliá, S; Masana, J; Alverez, A. Tetrahedron, 1983, 39, 1635; (d) Banfi, S; Colonna, S; Molinari, H; Juliá, S; Guixer, J. Tetrahedron, 1984, 40, 5207; (e) Bezuidenhoudt, B.C.B; Swanepoel, A; Augustyn, J.A.N; Ferreira, D. Tetrahedron Lett., 1987, 28, 4857; (f) Itsuno, S; Sakakura, M; Ito, K. J. Org. Chem., 1990, 55, 6047; (g) Baures, P.W; Eggleston, D.S; Flisak, J.R; Gombatz, K.J; Lantos, I; Mendelson, W; Remich, J.J. Tetrahedron Lett., 1990, 31, 6501; (h) 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; (i) Lasterra-Sánchez, M.E; Roberts, S.M. J. Chem. Soc., Perkin Trans I, 1995, 1467; (j) 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; (k) 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; (l) 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; (m) 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; (n) Allen, J.V; Cappi, M.W; Kary, P.D; Roberts, S.M; Williamson, N.M; Wu, L.E. J. Chem. Soc., Perkin Trans. I, 1997, 3297; (o) Adger, B.M; Barkley, J.V; Bergeron, S; Cappi, M.W; Flowerdew, B.E; Jackson, M.P; McCague, R; Nugent, T.C; Roberts, S.M. J. Chem. Soc., Perkin Trans. I, 1997, 3501; (p) Cappi, M.W; Chen, W.-P; Flood, R.W; Liao, Y.-W; Roberts, S.M; Skidmore, J; Smith, J. A; Williamson, N.M. Chem. Commun., 1998, 1159.
17. 3. (a) Juliá, S; Masana, J.; Vega, J.C. Angew. Chem. Int. Ed. Engl., 1980, 19, 929; (b) Juliá, S; Guixer, J; Masana, J; Rocas, J; Colonna, S; Annunziata, R; Molinari, H. J. Chem. Soc., Perkin Trans I, 1982, 1317; (c) Colonna, S; Molinari, H; Banfi, S; Juliá, S; Masana, J; Alverez, A. Tetrahedron, 1983, 39, 1635; (d) Banfi, S; Colonna, S; Molinari, H; Juliá, S; Guixer, J. Tetrahedron, 1984, 40, 5207; (e) Bezuidenhoudt, B.C.B; Swanepoel, A; Augustyn, J.A.N; Ferreira, D. Tetrahedron Lett., 1987, 28, 4857; (f) Itsuno, S; Sakakura, M; Ito, K. J. Org. Chem., 1990, 55, 6047; (g) Baures, P.W; Eggleston, D.S; Flisak, J.R; Gombatz, K.J; Lantos, I; Mendelson, W; Remich, J.J. Tetrahedron Lett., 1990, 31, 6501; (h) 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; (i) Lasterra-Sánchez, M.E; Roberts, S.M. J. Chem. Soc., Perkin Trans I, 1995, 1467; (j) 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; (k) 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; (l) 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; (m) 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; (n) Allen, J.V; Cappi, M.W; Kary, P.D; Roberts, S.M; Williamson, N.M; Wu, L.E. J. Chem. Soc., Perkin Trans. I, 1997, 3297; (o) Adger, B.M; Barkley, J.V; Bergeron, S; Cappi, M.W; Flowerdew, B.E; Jackson, M.P; McCague, R; Nugent, T.C; Roberts, S.M. J. Chem. Soc., Perkin Trans. I, 1997, 3501; (p) Cappi, M.W; Chen, W.-P; Flood, R.W; Liao, Y.-W; Roberts, S.M; Skidmore, J; Smith, J. A; Williamson, N.M. Chem. Commun., 1998, 1159.
18. 3. (a) Juliá, S; Masana, J.; Vega, J.C. Angew. Chem. Int. Ed. Engl., 1980, 19, 929; (b) Juliá, S; Guixer, J; Masana, J; Rocas, J; Colonna, S; Annunziata, R; Molinari, H. J. Chem. Soc., Perkin Trans I, 1982, 1317; (c) Colonna, S; Molinari, H; Banfi, S; Juliá, S; Masana, J; Alverez, A. Tetrahedron, 1983, 39, 1635; (d) Banfi, S; Colonna, S; Molinari, H; Juliá, S; Guixer, J. Tetrahedron, 1984, 40, 5207; (e) Bezuidenhoudt, B.C.B; Swanepoel, A; Augustyn, J.A.N; Ferreira, D. Tetrahedron Lett., 1987, 28, 4857; (f) Itsuno, S; Sakakura, M; Ito, K. J. Org. Chem., 1990, 55, 6047; (g) Baures, P.W; Eggleston, D.S; Flisak, J.R; Gombatz, K.J; Lantos, I; Mendelson, W; Remich, J.J. Tetrahedron Lett., 1990, 31, 6501; (h) 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; (i) Lasterra-Sánchez, M.E; Roberts, S.M. J. Chem. Soc., Perkin Trans I, 1995, 1467; (j) 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; (k) 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; (l) 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; (m) 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; (n) Allen, J.V; Cappi, M.W; Kary, P.D; Roberts, S.M; Williamson, N.M; Wu, L.E. J. Chem. Soc., Perkin Trans. I, 1997, 3297; (o) Adger, B.M; Barkley, J.V; Bergeron, S; Cappi, M.W; Flowerdew, B.E; Jackson, M.P; McCague, R; Nugent, T.C; Roberts, S.M. J. Chem. Soc., Perkin Trans. I, 1997, 3501; (p) Cappi, M.W; Chen, W.-P; Flood, R.W; Liao, Y.-W; Roberts, S.M; Skidmore, J; Smith, J. A; Williamson, N.M. Chem. Commun., 1998, 1159.
19. 3. (a) Juliá, S; Masana, J.; Vega, J.C. Angew. Chem. Int. Ed. Engl., 1980, 19, 929; (b) Juliá, S; Guixer, J; Masana, J; Rocas, J; Colonna, S; Annunziata, R; Molinari, H. J. Chem. Soc., Perkin Trans I, 1982, 1317; (c) Colonna, S; Molinari, H; Banfi, S; Juliá, S; Masana, J; Alverez, A. Tetrahedron, 1983, 39, 1635; (d) Banfi, S; Colonna, S; Molinari, H; Juliá, S; Guixer, J. Tetrahedron, 1984, 40, 5207; (e) Bezuidenhoudt, B.C.B; Swanepoel, A; Augustyn, J.A.N; Ferreira, D. Tetrahedron Lett., 1987, 28, 4857; (f) Itsuno, S; Sakakura, M; Ito, K. J. Org. Chem., 1990, 55, 6047; (g) Baures, P.W; Eggleston, D.S; Flisak, J.R; Gombatz, K.J; Lantos, I; Mendelson, W; Remich, J.J. Tetrahedron Lett., 1990, 31, 6501; (h) 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; (i) Lasterra-Sánchez, M.E; Roberts, S.M. J. Chem. Soc., Perkin Trans I, 1995, 1467; (j) 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; (k) 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; (l) 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; (m) 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; (n) Allen, J.V; Cappi, M.W; Kary, P.D; Roberts, S.M; Williamson, N.M; Wu, L.E. J. Chem. Soc., Perkin Trans. I, 1997, 3297; (o) Adger, B.M; Barkley, J.V; Bergeron, S; Cappi, M.W; Flowerdew, B.E; Jackson, M.P; McCague, R; Nugent, T.C; Roberts, S.M. J. Chem. Soc., Perkin Trans. I, 1997, 3501; (p) Cappi, M.W; Chen, W.-P; Flood, R.W; Liao, Y.-W; Roberts, S.M; Skidmore, J; Smith, J. A; Williamson, N.M. Chem. Commun., 1998, 1159.
20. 3. (a) Juliá, S; Masana, J.; Vega, J.C. Angew. Chem. Int. Ed. Engl., 1980, 19, 929; (b) Juliá, S; Guixer, J; Masana, J; Rocas, J; Colonna, S; Annunziata, R; Molinari, H. J. Chem. Soc., Perkin Trans I, 1982, 1317; (c) Colonna, S; Molinari, H; Banfi, S; Juliá, S; Masana, J; Alverez, A. Tetrahedron, 1983, 39, 1635; (d) Banfi, S; Colonna, S; Molinari, H; Juliá, S; Guixer, J. Tetrahedron, 1984, 40, 5207; (e) Bezuidenhoudt, B.C.B; Swanepoel, A; Augustyn, J.A.N; Ferreira, D. Tetrahedron Lett., 1987, 28, 4857; (f) Itsuno, S; Sakakura, M; Ito, K. J. Org. Chem., 1990, 55, 6047; (g) Baures, P.W; Eggleston, D.S; Flisak, J.R; Gombatz, K.J; Lantos, I; Mendelson, W; Remich, J.J. Tetrahedron Lett., 1990, 31, 6501; (h) 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; (i) Lasterra-Sánchez, M.E; Roberts, S.M. J. Chem. Soc., Perkin Trans I, 1995, 1467; (j) 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; (k) 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; (l) 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; (m) 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; (n) Allen, J.V; Cappi, M.W; Kary, P.D; Roberts, S.M; Williamson, N.M; Wu, L.E. J. Chem. Soc., Perkin Trans. I, 1997, 3297; (o) Adger, B.M; Barkley, J.V; Bergeron, S; Cappi, M.W; Flowerdew, B.E; Jackson, M.P; McCague, R; Nugent, T.C; Roberts, S.M. J. Chem. Soc., Perkin Trans. I, 1997, 3501; (p) Cappi, M.W; Chen, W.-P; Flood, R.W; Liao, Y.-W; Roberts, S.M; Skidmore, J; Smith, J. A; Williamson, N.M. Chem. Commun., 1998, 1159.
21. 4. Bougauchi, M; Watanabe, S; Arai, T; Sasai, H; Shibasaki, M. J. Am. Chem. Soc., 1997, 119, 2329; Daikai, K; Kamaura, M; Inanaga, J. Tetrahedron Lett., 1998, 39, 7321; Watanabe, S; Kobayashi, Y; Arai, T; Sasai, H; Bougauchi, M; Shibasaki, Tetrahedron Lett., 1998, 39, 7353.
22. 4. Bougauchi, M; Watanabe, S; Arai, T; Sasai, H; Shibasaki, M. J. Am. Chem. Soc., 1997, 119, 2329; Daikai, K; Kamaura, M; Inanaga, J. Tetrahedron Lett., 1998, 39, 7321; Watanabe, S; Kobayashi, Y; Arai, T; Sasai, H; Bougauchi, M; Shibasaki, Tetrahedron Lett., 1998, 39, 7353.
23. 4. Bougauchi, M; Watanabe, S; Arai, T; Sasai, H; Shibasaki, M. J. Am. Chem. Soc., 1997, 119, 2329; Daikai, K; Kamaura, M; Inanaga, J. Tetrahedron Lett., 1998, 39, 7321; Watanabe, S; Kobayashi, Y; Arai, T; Sasai, H; Bougauchi, M; Shibasaki, Tetrahedron Lett., 1998, 39, 7353.
24. 5. Elston, C.L; Jackson, R.W.F; MacDonald, S.J.F; Murray, P.J. Angew. Chem. Int. Ed. Engl., 1997, 36, 410.
25. 6. Baccin, C; Gusso, A; Pinna, F; Strukul, G. Organomet., 1995, 14, 1161.
26. 7. See for example: (a) Helder, R; Hummelen, J.C; Laane, R.W.P.M; Wiering, J.S; Wynberg, H. Tetrahedron Lett., 1976, 1831; (b) Hummelen, J.C; Wynberg, H. Tetrahedron Lett., 1978, 1089; (c) Wynberg, H; Greijdanus, B. J. Chem. Soc., Chem. Commun., 1978, 427; (d) Wynberg, H; Marsman, B. J. Org. Chem., 1980, 45, 158; (e) Pluim, H; Wynberg, H. J. Org. Chem., 1980, 45, 2498; (f) Harigaya, Y; Yamaguchi, H; Onda, M. Heterocycles, 1981, 15, 183; (g) Mazaleyrat, J.P. Tetrahedron Lett., 1983, 24, 1243; (h) Baba, N; Oda, J; Kawaguchi, M; Agric. Biol. Chem., 1986, 50, 3113; (i) Baba, N; Oda, J; Kawahara, S; Hamada, M. Bull. Inst. Chem. Res., Kyoto Univ., 1989, 67, 121; (j) Shi, M; Masaki, Y. J. Chem. Res. (S), 1994, 250; (k) Shi, M; Kazuta, K; Satoh, Y; Masaki, Y. Chem. Pharm. Bull., 1994, 42, 2625; (l) Macdonald G; Alcaraz L; Lewis N.J; Taylor R.J.K. Tetrahedron Lett., 1998, 39, 5433; (m) Arai, S; Oku, M; Miura, M; Shioiri, T. Synlett, 1998, 1201; (n) Watanabe, S; Arai, T; Sasai, H; Bougauchi, M; Shibasaki, M. J. Org. Chem., 1998, 63, 8090.
27. 7. See for example: (a) Helder, R; Hummelen, J.C; Laane, R.W.P.M; Wiering, J.S; Wynberg, H. Tetrahedron Lett., 1976, 1831; (b) Hummelen, J.C; Wynberg, H. Tetrahedron Lett., 1978, 1089; (c) Wynberg, H; Greijdanus, B. J. Chem. Soc., Chem. Commun., 1978, 427; (d) Wynberg, H; Marsman, B. J. Org. Chem., 1980, 45, 158; (e) Pluim, H; Wynberg, H. J. Org. Chem., 1980, 45, 2498; (f) Harigaya, Y; Yamaguchi, H; Onda, M. Heterocycles, 1981, 15, 183; (g) Mazaleyrat, J.P. Tetrahedron Lett., 1983, 24, 1243; (h) Baba, N; Oda, J; Kawaguchi, M; Agric. Biol. Chem., 1986, 50, 3113; (i) Baba, N; Oda, J; Kawahara, S; Hamada, M. Bull. Inst. Chem. Res., Kyoto Univ., 1989, 67, 121; (j) Shi, M; Masaki, Y. J. Chem. Res. (S), 1994, 250; (k) Shi, M; Kazuta, K; Satoh, Y; Masaki, Y. Chem. Pharm. Bull., 1994, 42, 2625; (l) Macdonald G; Alcaraz L; Lewis N.J; Taylor R.J.K. Tetrahedron Lett., 1998, 39, 5433; (m) Arai, S; Oku, M; Miura, M; Shioiri, T. Synlett, 1998, 1201; (n) Watanabe, S; Arai, T; Sasai, H; Bougauchi, M; Shibasaki, M. J. Org. Chem., 1998, 63, 8090.
28. 7. See for example: (a) Helder, R; Hummelen, J.C; Laane, R.W.P.M; Wiering, J.S; Wynberg, H. Tetrahedron Lett., 1976, 1831; (b) Hummelen, J.C; Wynberg, H. Tetrahedron Lett., 1978, 1089; (c) Wynberg, H; Greijdanus, B. J. Chem. Soc., Chem. Commun., 1978, 427; (d) Wynberg, H; Marsman, B. J. Org. Chem., 1980, 45, 158; (e) Pluim, H; Wynberg, H. J. Org. Chem., 1980, 45, 2498; (f) Harigaya, Y; Yamaguchi, H; Onda, M. Heterocycles, 1981, 15, 183; (g) Mazaleyrat, J.P. Tetrahedron Lett., 1983, 24, 1243; (h) Baba, N; Oda, J; Kawaguchi, M; Agric. Biol. Chem., 1986, 50, 3113; (i) Baba, N; Oda, J; Kawahara, S; Hamada, M. Bull. Inst. Chem. Res., Kyoto Univ., 1989, 67, 121; (j) Shi, M; Masaki, Y. J. Chem. Res. (S), 1994, 250; (k) Shi, M; Kazuta, K; Satoh, Y; Masaki, Y. Chem. Pharm. Bull., 1994, 42, 2625; (l) Macdonald G; Alcaraz L; Lewis N.J; Taylor R.J.K. Tetrahedron Lett., 1998, 39, 5433; (m) Arai, S; Oku, M; Miura, M; Shioiri, T. Synlett, 1998, 1201; (n) Watanabe, S; Arai, T; Sasai, H; Bougauchi, M; Shibasaki, M. J. Org. Chem., 1998, 63, 8090.
29. 7. See for example: (a) Helder, R; Hummelen, J.C; Laane, R.W.P.M; Wiering, J.S; Wynberg, H. Tetrahedron Lett., 1976, 1831; (b) Hummelen, J.C; Wynberg, H. Tetrahedron Lett., 1978, 1089; (c) Wynberg, H; Greijdanus, B. J. Chem. Soc., Chem. Commun., 1978, 427; (d) Wynberg, H; Marsman, B. J. Org. Chem., 1980, 45, 158; (e) Pluim, H; Wynberg, H. J. Org. Chem., 1980, 45, 2498; (f) Harigaya, Y; Yamaguchi, H; Onda, M. Heterocycles, 1981, 15, 183; (g) Mazaleyrat, J.P. Tetrahedron Lett., 1983, 24, 1243; (h) Baba, N; Oda, J; Kawaguchi, M; Agric. Biol. Chem., 1986, 50, 3113; (i) Baba, N; Oda, J; Kawahara, S; Hamada, M. Bull. Inst. Chem. Res., Kyoto Univ., 1989, 67, 121; (j) Shi, M; Masaki, Y. J. Chem. Res. (S), 1994, 250; (k) Shi, M; Kazuta, K; Satoh, Y; Masaki, Y. Chem. Pharm. Bull., 1994, 42, 2625; (l) Macdonald G; Alcaraz L; Lewis N.J; Taylor R.J.K. Tetrahedron Lett., 1998, 39, 5433; (m) Arai, S; Oku, M; Miura, M; Shioiri, T. Synlett, 1998, 1201; (n) Watanabe, S; Arai, T; Sasai, H; Bougauchi, M; Shibasaki, M. J. Org. Chem., 1998, 63, 8090.
30. 7. See for example: (a) Helder, R; Hummelen, J.C; Laane, R.W.P.M; Wiering, J.S; Wynberg, H. Tetrahedron Lett., 1976, 1831; (b) Hummelen, J.C; Wynberg, H. Tetrahedron Lett., 1978, 1089; (c) Wynberg, H; Greijdanus, B. J. Chem. Soc., Chem. Commun., 1978, 427; (d) Wynberg, H; Marsman, B. J. Org. Chem., 1980, 45, 158; (e) Pluim, H; Wynberg, H. J. Org. Chem., 1980, 45, 2498; (f) Harigaya, Y; Yamaguchi, H; Onda, M. Heterocycles, 1981, 15, 183; (g) Mazaleyrat, J.P. Tetrahedron Lett., 1983, 24, 1243; (h) Baba, N; Oda, J; Kawaguchi, M; Agric. Biol. Chem., 1986, 50, 3113; (i) Baba, N; Oda, J; Kawahara, S; Hamada, M. Bull. Inst. Chem. Res., Kyoto Univ., 1989, 67, 121; (j) Shi, M; Masaki, Y. J. Chem. Res. (S), 1994, 250; (k) Shi, M; Kazuta, K; Satoh, Y; Masaki, Y. Chem. Pharm. Bull., 1994, 42, 2625; (l) Macdonald G; Alcaraz L; Lewis N.J; Taylor R.J.K. Tetrahedron Lett., 1998, 39, 5433; (m) Arai, S; Oku, M; Miura, M; Shioiri, T. Synlett, 1998, 1201; (n) Watanabe, S; Arai, T; Sasai, H; Bougauchi, M; Shibasaki, M. J. Org. Chem., 1998, 63, 8090.
31. 7. See for example: (a) Helder, R; Hummelen, J.C; Laane, R.W.P.M; Wiering, J.S; Wynberg, H. Tetrahedron Lett., 1976, 1831; (b) Hummelen, J.C; Wynberg, H. Tetrahedron Lett., 1978, 1089; (c) Wynberg, H; Greijdanus, B. J. Chem. Soc., Chem. Commun., 1978, 427; (d) Wynberg, H; Marsman, B. J. Org. Chem., 1980, 45, 158; (e) Pluim, H; Wynberg, H. J. Org. Chem., 1980, 45, 2498; (f) Harigaya, Y; Yamaguchi, H; Onda, M. Heterocycles, 1981, 15, 183; (g) Mazaleyrat, J.P. Tetrahedron Lett., 1983, 24, 1243; (h) Baba, N; Oda, J; Kawaguchi, M; Agric. Biol. Chem., 1986, 50, 3113; (i) Baba, N; Oda, J; Kawahara, S; Hamada, M. Bull. Inst. Chem. Res., Kyoto Univ., 1989, 67, 121; (j) Shi, M; Masaki, Y. J. Chem. Res. (S), 1994, 250; (k) Shi, M; Kazuta, K; Satoh, Y; Masaki, Y. Chem. Pharm. Bull., 1994, 42, 2625; (l) Macdonald G; Alcaraz L; Lewis N.J; Taylor R.J.K. Tetrahedron Lett., 1998, 39, 5433; (m) Arai, S; Oku, M; Miura, M; Shioiri, T. Synlett, 1998, 1201; (n) Watanabe, S; Arai, T; Sasai, H; Bougauchi, M; Shibasaki, M. J. Org. Chem., 1998, 63, 8090.
32. 7. See for example: (a) Helder, R; Hummelen, J.C; Laane, R.W.P.M; Wiering, J.S; Wynberg, H. Tetrahedron Lett., 1976, 1831; (b) Hummelen, J.C; Wynberg, H. Tetrahedron Lett., 1978, 1089; (c) Wynberg, H; Greijdanus, B. J. Chem. Soc., Chem. Commun., 1978, 427; (d) Wynberg, H; Marsman, B. J. Org. Chem., 1980, 45, 158; (e) Pluim, H; Wynberg, H. J. Org. Chem., 1980, 45, 2498; (f) Harigaya, Y; Yamaguchi, H; Onda, M. Heterocycles, 1981, 15, 183; (g) Mazaleyrat, J.P. Tetrahedron Lett., 1983, 24, 1243; (h) Baba, N; Oda, J; Kawaguchi, M; Agric. Biol. Chem., 1986, 50, 3113; (i) Baba, N; Oda, J; Kawahara, S; Hamada, M. Bull. Inst. Chem. Res., Kyoto Univ., 1989, 67, 121; (j) Shi, M; Masaki, Y. J. Chem. Res. (S), 1994, 250; (k) Shi, M; Kazuta, K; Satoh, Y; Masaki, Y. Chem. Pharm. Bull., 1994, 42, 2625; (l) Macdonald G; Alcaraz L; Lewis N.J; Taylor R.J.K. Tetrahedron Lett., 1998, 39, 5433; (m) Arai, S; Oku, M; Miura, M; Shioiri, T. Synlett, 1998, 1201; (n) Watanabe, S; Arai, T; Sasai, H; Bougauchi, M; Shibasaki, M. J. Org. Chem., 1998, 63, 8090.
33. 7. See for example: (a) Helder, R; Hummelen, J.C; Laane, R.W.P.M; Wiering, J.S; Wynberg, H. Tetrahedron Lett., 1976, 1831; (b) Hummelen, J.C; Wynberg, H. Tetrahedron Lett., 1978, 1089; (c) Wynberg, H; Greijdanus, B. J. Chem. Soc., Chem. Commun., 1978, 427; (d) Wynberg, H; Marsman, B. J. Org. Chem., 1980, 45, 158; (e) Pluim, H; Wynberg, H. J. Org. Chem., 1980, 45, 2498; (f) Harigaya, Y; Yamaguchi, H; Onda, M. Heterocycles, 1981, 15, 183; (g) Mazaleyrat, J.P. Tetrahedron Lett., 1983, 24, 1243; (h) Baba, N; Oda, J; Kawaguchi, M; Agric. Biol. Chem., 1986, 50, 3113; (i) Baba, N; Oda, J; Kawahara, S; Hamada, M. Bull. Inst. Chem. Res., Kyoto Univ., 1989, 67, 121; (j) Shi, M; Masaki, Y. J. Chem. Res. (S), 1994, 250; (k) Shi, M; Kazuta, K; Satoh, Y; Masaki, Y. Chem. Pharm. Bull., 1994, 42, 2625; (l) Macdonald G; Alcaraz L; Lewis N.J; Taylor R.J.K. Tetrahedron Lett., 1998, 39, 5433; (m) Arai, S; Oku, M; Miura, M; Shioiri, T. Synlett, 1998, 1201; (n) Watanabe, S; Arai, T; Sasai, H; Bougauchi, M; Shibasaki, M. J. Org. Chem., 1998, 63, 8090.
34. 7. See for example: (a) Helder, R; Hummelen, J.C; Laane, R.W.P.M; Wiering, J.S; Wynberg, H. Tetrahedron Lett., 1976, 1831; (b) Hummelen, J.C; Wynberg, H. Tetrahedron Lett., 1978, 1089; (c) Wynberg, H; Greijdanus, B. J. Chem. Soc., Chem. Commun., 1978, 427; (d) Wynberg, H; Marsman, B. J. Org. Chem., 1980, 45, 158; (e) Pluim, H; Wynberg, H. J. Org. Chem., 1980, 45, 2498; (f) Harigaya, Y; Yamaguchi, H; Onda, M. Heterocycles, 1981, 15, 183; (g) Mazaleyrat, J.P. Tetrahedron Lett., 1983, 24, 1243; (h) Baba, N; Oda, J; Kawaguchi, M; Agric. Biol. Chem., 1986, 50, 3113; (i) Baba, N; Oda, J; Kawahara, S; Hamada, M. Bull. Inst. Chem. Res., Kyoto Univ., 1989, 67, 121; (j) Shi, M; Masaki, Y. J. Chem. Res. (S), 1994, 250; (k) Shi, M; Kazuta, K; Satoh, Y; Masaki, Y. Chem. Pharm. Bull., 1994, 42, 2625; (l) Macdonald G; Alcaraz L; Lewis N.J; Taylor R.J.K. Tetrahedron Lett., 1998, 39, 5433; (m) Arai, S; Oku, M; Miura, M; Shioiri, T. Synlett, 1998, 1201; (n) Watanabe, S; Arai, T; Sasai, H; Bougauchi, M; Shibasaki, M. J. Org. Chem., 1998, 63, 8090.
35. 7. See for example: (a) Helder, R; Hummelen, J.C; Laane, R.W.P.M; Wiering, J.S; Wynberg, H. Tetrahedron Lett., 1976, 1831; (b) Hummelen, J.C; Wynberg, H. Tetrahedron Lett., 1978, 1089; (c) Wynberg, H; Greijdanus, B. J. Chem. Soc., Chem. Commun., 1978, 427; (d) Wynberg, H; Marsman, B. J. Org. Chem., 1980, 45, 158; (e) Pluim, H; Wynberg, H. J. Org. Chem., 1980, 45, 2498; (f) Harigaya, Y; Yamaguchi, H; Onda, M. Heterocycles, 1981, 15, 183; (g) Mazaleyrat, J.P. Tetrahedron Lett., 1983, 24, 1243; (h) Baba, N; Oda, J; Kawaguchi, M; Agric. Biol. Chem., 1986, 50, 3113; (i) Baba, N; Oda, J; Kawahara, S; Hamada, M. Bull. Inst. Chem. Res., Kyoto Univ., 1989, 67, 121; (j) Shi, M; Masaki, Y. J. Chem. Res. (S), 1994, 250; (k) Shi, M; Kazuta, K; Satoh, Y; Masaki, Y. Chem. Pharm. Bull., 1994, 42, 2625; (l) Macdonald G; Alcaraz L; Lewis N.J; Taylor R.J.K. Tetrahedron Lett., 1998, 39, 5433; (m) Arai, S; Oku, M; Miura, M; Shioiri, T. Synlett, 1998, 1201; (n) Watanabe, S; Arai, T; Sasai, H; Bougauchi, M; Shibasaki, M. J. Org. Chem., 1998, 63, 8090.
36. 7. See for example: (a) Helder, R; Hummelen, J.C; Laane, R.W.P.M; Wiering, J.S; Wynberg, H. Tetrahedron Lett., 1976, 1831; (b) Hummelen, J.C; Wynberg, H. Tetrahedron Lett., 1978, 1089; (c) Wynberg, H; Greijdanus, B. J. Chem. Soc., Chem. Commun., 1978, 427; (d) Wynberg, H; Marsman, B. J. Org. Chem., 1980, 45, 158; (e) Pluim, H; Wynberg, H. J. Org. Chem., 1980, 45, 2498; (f) Harigaya, Y; Yamaguchi, H; Onda, M. Heterocycles, 1981, 15, 183; (g) Mazaleyrat, J.P. Tetrahedron Lett., 1983, 24, 1243; (h) Baba, N; Oda, J; Kawaguchi, M; Agric. Biol. Chem., 1986, 50, 3113; (i) Baba, N; Oda, J; Kawahara, S; Hamada, M. Bull. Inst. Chem. Res., Kyoto Univ., 1989, 67, 121; (j) Shi, M; Masaki, Y. J. Chem. Res. (S), 1994, 250; (k) Shi, M; Kazuta, K; Satoh, Y; Masaki, Y. Chem. Pharm. Bull., 1994, 42, 2625; (l) Macdonald G; Alcaraz L; Lewis N.J; Taylor R.J.K. Tetrahedron Lett., 1998, 39, 5433; (m) Arai, S; Oku, M; Miura, M; Shioiri, T. Synlett, 1998, 1201; (n) Watanabe, S; Arai, T; Sasai, H; Bougauchi, M; Shibasaki, M. J. Org. Chem., 1998, 63, 8090.
37. 7. See for example: (a) Helder, R; Hummelen, J.C; Laane, R.W.P.M; Wiering, J.S; Wynberg, H. Tetrahedron Lett., 1976, 1831; (b) Hummelen, J.C; Wynberg, H. Tetrahedron Lett., 1978, 1089; (c) Wynberg, H; Greijdanus, B. J. Chem. Soc., Chem. Commun., 1978, 427; (d) Wynberg, H; Marsman, B. J. Org. Chem., 1980, 45, 158; (e) Pluim, H; Wynberg, H. J. Org. Chem., 1980, 45, 2498; (f) Harigaya, Y; Yamaguchi, H; Onda, M. Heterocycles, 1981, 15, 183; (g) Mazaleyrat, J.P. Tetrahedron Lett., 1983, 24, 1243; (h) Baba, N; Oda, J; Kawaguchi, M; Agric. Biol. Chem., 1986, 50, 3113; (i) Baba, N; Oda, J; Kawahara, S; Hamada, M. Bull. Inst. Chem. Res., Kyoto Univ., 1989, 67, 121; (j) Shi, M; Masaki, Y. J. Chem. Res. (S), 1994, 250; (k) Shi, M; Kazuta, K; Satoh, Y; Masaki, Y. Chem. Pharm. Bull., 1994, 42, 2625; (l) Macdonald G; Alcaraz L; Lewis N.J; Taylor R.J.K. Tetrahedron Lett., 1998, 39, 5433; (m) Arai, S; Oku, M; Miura, M; Shioiri, T. Synlett, 1998, 1201; (n) Watanabe, S; Arai, T; Sasai, H; Bougauchi, M; Shibasaki, M. J. Org. Chem., 1998, 63, 8090.
38. 7. See for example: (a) Helder, R; Hummelen, J.C; Laane, R.W.P.M; Wiering, J.S; Wynberg, H. Tetrahedron Lett., 1976, 1831; (b) Hummelen, J.C; Wynberg, H. Tetrahedron Lett., 1978, 1089; (c) Wynberg, H; Greijdanus, B. J. Chem. Soc., Chem. Commun., 1978, 427; (d) Wynberg, H; Marsman, B. J. Org. Chem., 1980, 45, 158; (e) Pluim, H; Wynberg, H. J. Org. Chem., 1980, 45, 2498; (f) Harigaya, Y; Yamaguchi, H; Onda, M. Heterocycles, 1981, 15, 183; (g) Mazaleyrat, J.P. Tetrahedron Lett., 1983, 24, 1243; (h) Baba, N; Oda, J; Kawaguchi, M; Agric. Biol. Chem., 1986, 50, 3113; (i) Baba, N; Oda, J; Kawahara, S; Hamada, M. Bull. Inst. Chem. Res., Kyoto Univ., 1989, 67, 121; (j) Shi, M; Masaki, Y. J. Chem. Res. (S), 1994, 250; (k) Shi, M; Kazuta, K; Satoh, Y; Masaki, Y. Chem. Pharm. Bull., 1994, 42, 2625; (l) Macdonald G; Alcaraz L; Lewis N.J; Taylor R.J.K. Tetrahedron Lett., 1998, 39, 5433; (m) Arai, S; Oku, M; Miura, M; Shioiri, T. Synlett, 1998, 1201; (n) Watanabe, S; Arai, T; Sasai, H; Bougauchi, M; Shibasaki, M. J. Org. Chem., 1998, 63, 8090.
39. 7. See for example: (a) Helder, R; Hummelen, J.C; Laane, R.W.P.M; Wiering, J.S; Wynberg, H. Tetrahedron Lett., 1976, 1831; (b) Hummelen, J.C; Wynberg, H. Tetrahedron Lett., 1978, 1089; (c) Wynberg, H; Greijdanus, B. J. Chem. Soc., Chem. Commun., 1978, 427; (d) Wynberg, H; Marsman, B. J. Org. Chem., 1980, 45, 158; (e) Pluim, H; Wynberg, H. J. Org. Chem., 1980, 45, 2498; (f) Harigaya, Y; Yamaguchi, H; Onda, M. Heterocycles, 1981, 15, 183; (g) Mazaleyrat, J.P. Tetrahedron Lett., 1983, 24, 1243; (h) Baba, N; Oda, J; Kawaguchi, M; Agric. Biol. Chem., 1986, 50, 3113; (i) Baba, N; Oda, J; Kawahara, S; Hamada, M. Bull. Inst. Chem. Res., Kyoto Univ., 1989, 67, 121; (j) Shi, M; Masaki, Y. J. Chem. Res. (S), 1994, 250; (k) Shi, M; Kazuta, K; Satoh, Y; Masaki, Y. Chem. Pharm. Bull., 1994, 42, 2625; (l) Macdonald G; Alcaraz L; Lewis N.J; Taylor R.J.K. Tetrahedron Lett., 1998, 39, 5433; (m) Arai, S; Oku, M; Miura, M; Shioiri, T. Synlett, 1998, 1201; (n) Watanabe, S; Arai, T; Sasai, H; Bougauchi, M; Shibasaki, M. J. Org. Chem., 1998, 63, 8090.
40. 8. For the enantioselective preparation of epoxides of type 2 via asymmetric phase-transfer catalysed Darzens reaction see Arai, S; Ishida, T; Shioiri, T. Tetrahedron Lett., 1998, 39, 8299 and references therein.
41. 9. For preliminary communication on the use of N-anthracenylmethyl substituted cinchona alkaloids in the highly enantioselective epoxidation of α, β-unsaturated ketones see: Lygo, B; Wainwright, P.G. Tetrahedron Lett., 1998, 39, 1599.
42. 10. For the use of N-[4-(iodo)benzyl]cinchoninium bromide in the highly enantioselective epoxidation of α, β-unsaturated ketones see: Arai, S; Tsuge, H; Shioiri, T. Tetrahedron Lett., 1998, 39, 7563.
43. 11. Lygo, B; Wainwright, P.G. Tetrahedron Lett., 1997, 38, 8595; Corey, E.J; Xu, F; Noe, M.C. J. Am. Chem. Soc., 1997, 119, 12414; Corey, E.J; Noe, M.C; Xu, F. Tetrahedron Lett., 1998, 39, 5347; O'Donnel, M.J; Delgado, F; Hostettler, C; Schwesinger, R. Tetrahedron Lett., 1998, 39, 8775.
44. 11. Lygo, B; Wainwright, P.G. Tetrahedron Lett., 1997, 38, 8595; Corey, E.J; Xu, F; Noe, M.C. J. Am. Chem. Soc., 1997, 119, 12414; Corey, E.J; Noe, M.C; Xu, F. Tetrahedron Lett., 1998, 39, 5347; O'Donnel, M.J; Delgado, F; Hostettler, C; Schwesinger, R. Tetrahedron Lett., 1998, 39, 8775.
45. 11. Lygo, B; Wainwright, P.G. Tetrahedron Lett., 1997, 38, 8595; Corey, E.J; Xu, F; Noe, M.C. J. Am. Chem. Soc., 1997, 119, 12414; Corey, E.J; Noe, M.C; Xu, F. Tetrahedron Lett., 1998, 39, 5347; O'Donnel, M.J; Delgado, F; Hostettler, C; Schwesinger, R. Tetrahedron Lett., 1998, 39, 8775.
46. 11. Lygo, B; Wainwright, P.G. Tetrahedron Lett., 1997, 38, 8595; Corey, E.J; Xu, F; Noe, M.C. J. Am. Chem. Soc., 1997, 119, 12414; Corey, E.J; Noe, M.C; Xu, F. Tetrahedron Lett., 1998, 39, 5347; O'Donnel, M.J; Delgado, F; Hostettler, C; Schwesinger, R. Tetrahedron Lett., 1998, 39, 8775.
47. 12. O'Donnell, M.J; Wu, S; Huffman, J.C. Tetrahedron, 1994, 50, 4507.
48. 13. The absolute stereochemistry depicted for the epoxide products 2 is based on the known stereochemistry of compound 2a. In these schemes it is assumed that the same sense of selectivity applies to the other substrates.
49. 14. If the reactions are terminated before complete consumption of the starting E-enones 1, significant amounts of the corresponding Z-alkene isomers can be detected. This suggests that isomerisation of the alkene geometry in the enone substrates occurs readily under the epoxidation conditions.
50. 15. The rate of epoxidation is dependant on the rate of stirring, and the efficiency of mixing of the two phase system, however rate of reaction does not appear to affect the enantioselectivity.
51. 16. Perrin, D.D; Armarego, W.L.F. "Purification of Laboratory Chemicals", 3rd Ed., Pergamon Press, Oxford, 1988.
52. 17. Kohler, E.P; Chadwell, H.M. Org. Synth. Col. Vol. I, 1932, 78.
53. 18. Chaffee, A.L; Cooke, R.G; Dagley, I.J; Perlmutter, P; Thomas, R.L. Aust. J. Chem., 1981, 34, 587.
54. 1H nmr spectra of the quaternary ammonium salts are concentration dependent, these data were recorded on solutions containing 40mg/ml.