Synthesis of β-Substituted-butenolides through the Palladium-Catalysed Reaction of Unsaturated Triflates and Halides with Methyl 4-Hydroxy-2-butenoate

Synlett

Volumn 1996, Issue 6, 1996, Pages 545-546

  Cacchi, Sandro ^a   Ciattini, Pier Giuseppe ^a   Morera, Enrico ^a   Pace, Paola ^a  

^a SAPIENZA UNIVERSITY OF ROME   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002566517     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5471     Document Type: Article

References (33)

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2. Hanessian, S., Murray, P.J., Sahoo, S.P. Tetrahedron Lett. 1985, 26, 5623; ibid 1985, 26, 5627; ibid 1985, 26, 5631; Herrmann, J.L., Berger, M.H., Schlessinger, R.H. J. Am. Chem. Soc. 1979, 101, 1544; Damon, R.E., Schlessinger, R.H. Tetrahedron Lett. 1976, 1561.
3. Hanessian, S., Murray, P.J., Sahoo, S.P. Tetrahedron Lett. 1985, 26, 5623; ibid 1985, 26, 5627; ibid 1985, 26, 5631; Herrmann, J.L., Berger, M.H., Schlessinger, R.H. J. Am. Chem. Soc. 1979, 101, 1544; Damon, R.E., Schlessinger, R.H. Tetrahedron Lett. 1976, 1561.
4. Hanessian, S., Murray, P.J., Sahoo, S.P. Tetrahedron Lett. 1985, 26, 5623; ibid 1985, 26, 5627; ibid 1985, 26, 5631; Herrmann, J.L., Berger, M.H., Schlessinger, R.H. J. Am. Chem. Soc. 1979, 101, 1544; Damon, R.E., Schlessinger, R.H. Tetrahedron Lett. 1976, 1561.
5. Hanessian, S., Murray, P.J., Sahoo, S.P. Tetrahedron Lett. 1985, 26, 5623; ibid 1985, 26, 5627; ibid 1985, 26, 5631; Herrmann, J.L., Berger, M.H., Schlessinger, R.H. J. Am. Chem. Soc. 1979, 101, 1544; Damon, R.E., Schlessinger, R.H. Tetrahedron Lett. 1976, 1561.
6. Hanessian, S., Murray, P.J., Sahoo, S.P. Tetrahedron Lett. 1985, 26, 5623; ibid 1985, 26, 5627; ibid 1985, 26, 5631; Herrmann, J.L., Berger, M.H., Schlessinger, R.H. J. Am. Chem. Soc. 1979, 101, 1544; Damon, R.E., Schlessinger, R.H. Tetrahedron Lett. 1976, 1561.
7. Knight, D.W. Contemporary Org. Synthesis 1994, 1, 287.
8. See for example: Matsushita, K., Komori, T., Oi, S., Inoue, Y. Tetrahedron Lett. 1994, 35, 5889; Arcadi, A., Cacchi, S., Fabrizi, G., Marinelli, F. Synlett 1993, 65; Hollingworth, G.J., Sweeney, J.B. Synlett 1993, 463; Annby, U., Stenkula, M., Andersson, C.-M. Tetrahedron Lett. 1993, 34, 8545; Hollingworth, G.J., Sweeney, J.B. Tetrahedron Lett. 1992, 33, 7049; El Ali, B., Alper, H. J. Org. Chem. 1991, 56, 5357; Larock, R.C., Stinn, D.E., Kuo, M.-Y. Tetrahedron Lett. 1990, 31, 17; Arcadi, A., Bernocchi, E., Burini, A., Cacchi, S., Marinelli, F., Pietroni, B. Tetrahedron Lett. 1989, 30, 3465; Arcadi, A., Bernocchi, E., Burini, A., Cacchi, S., Marinelli, F., Pietroni, B. Tetrahedron 1988, 44, 481; Ciattini, P.G., Ortar, G. Synthesis 1986, 70: Kobayashi, M., Negishi, E. J. Org. Chem. 1980, 45, 5223; Cowell, A., Stille, J.K. Tetrahedron Lett. 1979, 133.
9. See for example: Matsushita, K., Komori, T., Oi, S., Inoue, Y. Tetrahedron Lett. 1994, 35, 5889; Arcadi, A., Cacchi, S., Fabrizi, G., Marinelli, F. Synlett 1993, 65; Hollingworth, G.J., Sweeney, J.B. Synlett 1993, 463; Annby, U., Stenkula, M., Andersson, C.-M. Tetrahedron Lett. 1993, 34, 8545; Hollingworth, G.J., Sweeney, J.B. Tetrahedron Lett. 1992, 33, 7049; El Ali, B., Alper, H. J. Org. Chem. 1991, 56, 5357; Larock, R.C., Stinn, D.E., Kuo, M.-Y. Tetrahedron Lett. 1990, 31, 17; Arcadi, A., Bernocchi, E., Burini, A., Cacchi, S., Marinelli, F., Pietroni, B. Tetrahedron Lett. 1989, 30, 3465; Arcadi, A., Bernocchi, E., Burini, A., Cacchi, S., Marinelli, F., Pietroni, B. Tetrahedron 1988, 44, 481; Ciattini, P.G., Ortar, G. Synthesis 1986, 70: Kobayashi, M., Negishi, E. J. Org. Chem. 1980, 45, 5223; Cowell, A., Stille, J.K. Tetrahedron Lett. 1979, 133.
10. See for example: Matsushita, K., Komori, T., Oi, S., Inoue, Y. Tetrahedron Lett. 1994, 35, 5889; Arcadi, A., Cacchi, S., Fabrizi, G., Marinelli, F. Synlett 1993, 65; Hollingworth, G.J., Sweeney, J.B. Synlett 1993, 463; Annby, U., Stenkula, M., Andersson, C.-M. Tetrahedron Lett. 1993, 34, 8545; Hollingworth, G.J., Sweeney, J.B. Tetrahedron Lett. 1992, 33, 7049; El Ali, B., Alper, H. J. Org. Chem. 1991, 56, 5357; Larock, R.C., Stinn, D.E., Kuo, M.-Y. Tetrahedron Lett. 1990, 31, 17; Arcadi, A., Bernocchi, E., Burini, A., Cacchi, S., Marinelli, F., Pietroni, B. Tetrahedron Lett. 1989, 30, 3465; Arcadi, A., Bernocchi, E., Burini, A., Cacchi, S., Marinelli, F., Pietroni, B. Tetrahedron 1988, 44, 481; Ciattini, P.G., Ortar, G. Synthesis 1986, 70: Kobayashi, M., Negishi, E. J. Org. Chem. 1980, 45, 5223; Cowell, A., Stille, J.K. Tetrahedron Lett. 1979, 133.
11. See for example: Matsushita, K., Komori, T., Oi, S., Inoue, Y. Tetrahedron Lett. 1994, 35, 5889; Arcadi, A., Cacchi, S., Fabrizi, G., Marinelli, F. Synlett 1993, 65; Hollingworth, G.J., Sweeney, J.B. Synlett 1993, 463; Annby, U., Stenkula, M., Andersson, C.-M. Tetrahedron Lett. 1993, 34, 8545; Hollingworth, G.J., Sweeney, J.B. Tetrahedron Lett. 1992, 33, 7049; El Ali, B., Alper, H. J. Org. Chem. 1991, 56, 5357; Larock, R.C., Stinn, D.E., Kuo, M.-Y. Tetrahedron Lett. 1990, 31, 17; Arcadi, A., Bernocchi, E., Burini, A., Cacchi, S., Marinelli, F., Pietroni, B. Tetrahedron Lett. 1989, 30, 3465; Arcadi, A., Bernocchi, E., Burini, A., Cacchi, S., Marinelli, F., Pietroni, B. Tetrahedron 1988, 44, 481; Ciattini, P.G., Ortar, G. Synthesis 1986, 70: Kobayashi, M., Negishi, E. J. Org. Chem. 1980, 45, 5223; Cowell, A., Stille, J.K. Tetrahedron Lett. 1979, 133.
12. See for example: Matsushita, K., Komori, T., Oi, S., Inoue, Y. Tetrahedron Lett. 1994, 35, 5889; Arcadi, A., Cacchi, S., Fabrizi, G., Marinelli, F. Synlett 1993, 65; Hollingworth, G.J., Sweeney, J.B. Synlett 1993, 463; Annby, U., Stenkula, M., Andersson, C.-M. Tetrahedron Lett. 1993, 34, 8545; Hollingworth, G.J., Sweeney, J.B. Tetrahedron Lett. 1992, 33, 7049; El Ali, B., Alper, H. J. Org. Chem. 1991, 56, 5357; Larock, R.C., Stinn, D.E., Kuo, M.-Y. Tetrahedron Lett. 1990, 31, 17; Arcadi, A., Bernocchi, E., Burini, A., Cacchi, S., Marinelli, F., Pietroni, B. Tetrahedron Lett. 1989, 30, 3465; Arcadi, A., Bernocchi, E., Burini, A., Cacchi, S., Marinelli, F., Pietroni, B. Tetrahedron 1988, 44, 481; Ciattini, P.G., Ortar, G. Synthesis 1986, 70: Kobayashi, M., Negishi, E. J. Org. Chem. 1980, 45, 5223; Cowell, A., Stille, J.K. Tetrahedron Lett. 1979, 133.
13. See for example: Matsushita, K., Komori, T., Oi, S., Inoue, Y. Tetrahedron Lett. 1994, 35, 5889; Arcadi, A., Cacchi, S., Fabrizi, G., Marinelli, F. Synlett 1993, 65; Hollingworth, G.J., Sweeney, J.B. Synlett 1993, 463; Annby, U., Stenkula, M., Andersson, C.-M. Tetrahedron Lett. 1993, 34, 8545; Hollingworth, G.J., Sweeney, J.B. Tetrahedron Lett. 1992, 33, 7049; El Ali, B., Alper, H. J. Org. Chem. 1991, 56, 5357; Larock, R.C., Stinn, D.E., Kuo, M.-Y. Tetrahedron Lett. 1990, 31, 17; Arcadi, A., Bernocchi, E., Burini, A., Cacchi, S., Marinelli, F., Pietroni, B. Tetrahedron Lett. 1989, 30, 3465; Arcadi, A., Bernocchi, E., Burini, A., Cacchi, S., Marinelli, F., Pietroni, B. Tetrahedron 1988, 44, 481; Ciattini, P.G., Ortar, G. Synthesis 1986, 70: Kobayashi, M., Negishi, E. J. Org. Chem. 1980, 45, 5223; Cowell, A., Stille, J.K. Tetrahedron Lett. 1979, 133.
14. See for example: Matsushita, K., Komori, T., Oi, S., Inoue, Y. Tetrahedron Lett. 1994, 35, 5889; Arcadi, A., Cacchi, S., Fabrizi, G., Marinelli, F. Synlett 1993, 65; Hollingworth, G.J., Sweeney, J.B. Synlett 1993, 463; Annby, U., Stenkula, M., Andersson, C.-M. Tetrahedron Lett. 1993, 34, 8545; Hollingworth, G.J., Sweeney, J.B. Tetrahedron Lett. 1992, 33, 7049; El Ali, B., Alper, H. J. Org. Chem. 1991, 56, 5357; Larock, R.C., Stinn, D.E., Kuo, M.-Y. Tetrahedron Lett. 1990, 31, 17; Arcadi, A., Bernocchi, E., Burini, A., Cacchi, S., Marinelli, F., Pietroni, B. Tetrahedron Lett. 1989, 30, 3465; Arcadi, A., Bernocchi, E., Burini, A., Cacchi, S., Marinelli, F., Pietroni, B. Tetrahedron 1988, 44, 481; Ciattini, P.G., Ortar, G. Synthesis 1986, 70: Kobayashi, M., Negishi, E. J. Org. Chem. 1980, 45, 5223; Cowell, A., Stille, J.K. Tetrahedron Lett. 1979, 133.
15. See for example: Matsushita, K., Komori, T., Oi, S., Inoue, Y. Tetrahedron Lett. 1994, 35, 5889; Arcadi, A., Cacchi, S., Fabrizi, G., Marinelli, F. Synlett 1993, 65; Hollingworth, G.J., Sweeney, J.B. Synlett 1993, 463; Annby, U., Stenkula, M., Andersson, C.-M. Tetrahedron Lett. 1993, 34, 8545; Hollingworth, G.J., Sweeney, J.B. Tetrahedron Lett. 1992, 33, 7049; El Ali, B., Alper, H. J. Org. Chem. 1991, 56, 5357; Larock, R.C., Stinn, D.E., Kuo, M.-Y. Tetrahedron Lett. 1990, 31, 17; Arcadi, A., Bernocchi, E., Burini, A., Cacchi, S., Marinelli, F., Pietroni, B. Tetrahedron Lett. 1989, 30, 3465; Arcadi, A., Bernocchi, E., Burini, A., Cacchi, S., Marinelli, F., Pietroni, B. Tetrahedron 1988, 44, 481; Ciattini, P.G., Ortar, G. Synthesis 1986, 70: Kobayashi, M., Negishi, E. J. Org. Chem. 1980, 45, 5223; Cowell, A., Stille, J.K. Tetrahedron Lett. 1979, 133.
16. See for example: Matsushita, K., Komori, T., Oi, S., Inoue, Y. Tetrahedron Lett. 1994, 35, 5889; Arcadi, A., Cacchi, S., Fabrizi, G., Marinelli, F. Synlett 1993, 65; Hollingworth, G.J., Sweeney, J.B. Synlett 1993, 463; Annby, U., Stenkula, M., Andersson, C.-M. Tetrahedron Lett. 1993, 34, 8545; Hollingworth, G.J., Sweeney, J.B. Tetrahedron Lett. 1992, 33, 7049; El Ali, B., Alper, H. J. Org. Chem. 1991, 56, 5357; Larock, R.C., Stinn, D.E., Kuo, M.-Y. Tetrahedron Lett. 1990, 31, 17; Arcadi, A., Bernocchi, E., Burini, A., Cacchi, S., Marinelli, F., Pietroni, B. Tetrahedron Lett. 1989, 30, 3465; Arcadi, A., Bernocchi, E., Burini, A., Cacchi, S., Marinelli, F., Pietroni, B. Tetrahedron 1988, 44, 481; Ciattini, P.G., Ortar, G. Synthesis 1986, 70: Kobayashi, M., Negishi, E. J. Org. Chem. 1980, 45, 5223; Cowell, A., Stille, J.K. Tetrahedron Lett. 1979, 133.
17. See for example: Matsushita, K., Komori, T., Oi, S., Inoue, Y. Tetrahedron Lett. 1994, 35, 5889; Arcadi, A., Cacchi, S., Fabrizi, G., Marinelli, F. Synlett 1993, 65; Hollingworth, G.J., Sweeney, J.B. Synlett 1993, 463; Annby, U., Stenkula, M., Andersson, C.-M. Tetrahedron Lett. 1993, 34, 8545; Hollingworth, G.J., Sweeney, J.B. Tetrahedron Lett. 1992, 33, 7049; El Ali, B., Alper, H. J. Org. Chem. 1991, 56, 5357; Larock, R.C., Stinn, D.E., Kuo, M.-Y. Tetrahedron Lett. 1990, 31, 17; Arcadi, A., Bernocchi, E., Burini, A., Cacchi, S., Marinelli, F., Pietroni, B. Tetrahedron Lett. 1989, 30, 3465; Arcadi, A., Bernocchi, E., Burini, A., Cacchi, S., Marinelli, F., Pietroni, B. Tetrahedron 1988, 44, 481; Ciattini, P.G., Ortar, G. Synthesis 1986, 70: Kobayashi, M., Negishi, E. J. Org. Chem. 1980, 45, 5223; Cowell, A., Stille, J.K. Tetrahedron Lett. 1979, 133.
18. See for example: Matsushita, K., Komori, T., Oi, S., Inoue, Y. Tetrahedron Lett. 1994, 35, 5889; Arcadi, A., Cacchi, S., Fabrizi, G., Marinelli, F. Synlett 1993, 65; Hollingworth, G.J., Sweeney, J.B. Synlett 1993, 463; Annby, U., Stenkula, M., Andersson, C.-M. Tetrahedron Lett. 1993, 34, 8545; Hollingworth, G.J., Sweeney, J.B. Tetrahedron Lett. 1992, 33, 7049; El Ali, B., Alper, H. J. Org. Chem. 1991, 56, 5357; Larock, R.C., Stinn, D.E., Kuo, M.-Y. Tetrahedron Lett. 1990, 31, 17; Arcadi, A., Bernocchi, E., Burini, A., Cacchi, S., Marinelli, F., Pietroni, B. Tetrahedron Lett. 1989, 30, 3465; Arcadi, A., Bernocchi, E., Burini, A., Cacchi, S., Marinelli, F., Pietroni, B. Tetrahedron 1988, 44, 481; Ciattini, P.G., Ortar, G. Synthesis 1986, 70: Kobayashi, M., Negishi, E. J. Org. Chem. 1980, 45, 5223; Cowell, A., Stille, J.K. Tetrahedron Lett. 1979, 133.
19. See for example: Matsushita, K., Komori, T., Oi, S., Inoue, Y. Tetrahedron Lett. 1994, 35, 5889; Arcadi, A., Cacchi, S., Fabrizi, G., Marinelli, F. Synlett 1993, 65; Hollingworth, G.J., Sweeney, J.B. Synlett 1993, 463; Annby, U., Stenkula, M., Andersson, C.-M. Tetrahedron Lett. 1993, 34, 8545; Hollingworth, G.J., Sweeney, J.B. Tetrahedron Lett. 1992, 33, 7049; El Ali, B., Alper, H. J. Org. Chem. 1991, 56, 5357; Larock, R.C., Stinn, D.E., Kuo, M.-Y. Tetrahedron Lett. 1990, 31, 17; Arcadi, A., Bernocchi, E., Burini, A., Cacchi, S., Marinelli, F., Pietroni, B. Tetrahedron Lett. 1989, 30, 3465; Arcadi, A., Bernocchi, E., Burini, A., Cacchi, S., Marinelli, F., Pietroni, B. Tetrahedron 1988, 44, 481; Ciattini, P.G., Ortar, G. Synthesis 1986, 70: Kobayashi, M., Negishi, E. J. Org. Chem. 1980, 45, 5223; Cowell, A., Stille, J.K. Tetrahedron Lett. 1979, 133.
20. Harnisch, W., Morera, E., Ortar, G. J. Org. Chem. 1985, 50, 1990.
21. Arcadi, A., Cacchi, S., Fabrizi, G., Marinelli, F., Pace, P. submitted.
22. 8
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24. +, 100), 167 (38), 153 (91), 128 (48).
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27. Kang, S.-K., Jung, K.-Y., Park, C.-H., Namkoong, E.-Y., Kim, T.-H. Tetrahedron Lett. 1995, 36, 6287; Jeffery, T. Tetrahedron Lett. 1993, 34, 1133; Bernocchi, E., Cacchi, S., Ciattini, P.G., Morera, E., Ortar, G. Tetrahedron Lett. 1992, 33, 3073; Arcadi, A., Bernocchi, E., Cacchi, S., Marinelli, F. Tetrahedron 1991, 47, 1525; Jeffery, T. Tetrahedron Lett. 1991, 32, 2121; Mandai, T., Hasegawa, S., Fujimoto, T., Kawada, M., Nokami, J., Tsuji, J. Synlett 1990, 85.
28. Kang, S.-K., Jung, K.-Y., Park, C.-H., Namkoong, E.-Y., Kim, T.-H. Tetrahedron Lett. 1995, 36, 6287; Jeffery, T. Tetrahedron Lett. 1993, 34, 1133; Bernocchi, E., Cacchi, S., Ciattini, P.G., Morera, E., Ortar, G. Tetrahedron Lett. 1992, 33, 3073; Arcadi, A., Bernocchi, E., Cacchi, S., Marinelli, F. Tetrahedron 1991, 47, 1525; Jeffery, T. Tetrahedron Lett. 1991, 32, 2121; Mandai, T., Hasegawa, S., Fujimoto, T., Kawada, M., Nokami, J., Tsuji, J. Synlett 1990, 85.
29. Kang, S.-K., Jung, K.-Y., Park, C.-H., Namkoong, E.-Y., Kim, T.-H. Tetrahedron Lett. 1995, 36, 6287; Jeffery, T. Tetrahedron Lett. 1993, 34, 1133; Bernocchi, E., Cacchi, S., Ciattini, P.G., Morera, E., Ortar, G. Tetrahedron Lett. 1992, 33, 3073; Arcadi, A., Bernocchi, E., Cacchi, S., Marinelli, F. Tetrahedron 1991, 47, 1525; Jeffery, T. Tetrahedron Lett. 1991, 32, 2121; Mandai, T., Hasegawa, S., Fujimoto, T., Kawada, M., Nokami, J., Tsuji, J. Synlett 1990, 85.
30. Kang, S.-K., Jung, K.-Y., Park, C.-H., Namkoong, E.-Y., Kim, T.-H. Tetrahedron Lett. 1995, 36, 6287; Jeffery, T. Tetrahedron Lett. 1993, 34, 1133; Bernocchi, E., Cacchi, S., Ciattini, P.G., Morera, E., Ortar, G. Tetrahedron Lett. 1992, 33, 3073; Arcadi, A., Bernocchi, E., Cacchi, S., Marinelli, F. Tetrahedron 1991, 47, 1525; Jeffery, T. Tetrahedron Lett. 1991, 32, 2121; Mandai, T., Hasegawa, S., Fujimoto, T., Kawada, M., Nokami, J., Tsuji, J. Synlett 1990, 85.
31. Kang, S.-K., Jung, K.-Y., Park, C.-H., Namkoong, E.-Y., Kim, T.-H. Tetrahedron Lett. 1995, 36, 6287; Jeffery, T. Tetrahedron Lett. 1993, 34, 1133; Bernocchi, E., Cacchi, S., Ciattini, P.G., Morera, E., Ortar, G. Tetrahedron Lett. 1992, 33, 3073; Arcadi, A., Bernocchi, E., Cacchi, S., Marinelli, F. Tetrahedron 1991, 47, 1525; Jeffery, T. Tetrahedron Lett. 1991, 32, 2121; Mandai, T., Hasegawa, S., Fujimoto, T., Kawada, M., Nokami, J., Tsuji, J. Synlett 1990, 85.
32. Kang, S.-K., Jung, K.-Y., Park, C.-H., Namkoong, E.-Y., Kim, T.-H. Tetrahedron Lett. 1995, 36, 6287; Jeffery, T. Tetrahedron Lett. 1993, 34, 1133; Bernocchi, E., Cacchi, S., Ciattini, P.G., Morera, E., Ortar, G. Tetrahedron Lett. 1992, 33, 3073; Arcadi, A., Bernocchi, E., Cacchi, S., Marinelli, F. Tetrahedron 1991, 47, 1525; Jeffery, T. Tetrahedron Lett. 1991, 32, 2121; Mandai, T., Hasegawa, S., Fujimoto, T., Kawada, M., Nokami, J., Tsuji, J. Synlett 1990, 85.
33. The reaction of aryl or vinyl halides with 2 has been performed at 80°C according to the procedure described in ref. 9.