Reactive dienophiles containing a difluoromethylenephosphonato group

Chemical Communications

Volumn , Issue 12, 1996, Pages 1457-1458

  Blades, Kevin ^a   Lequeux, Thierry P ^a   Percy, Jonathan M ^a  

^a UNIVERSITY OF BIRMINGHAM   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 1842509108     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/cc9960001457     Document Type: Article

References (19)

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2. T. R. Burke, M. S. Smyth, A. Otaka, M. Nomizu, P. P. Roller, G. Wolf, R. Case and S. E. Shoelson, Biochemistry, 1994, 33, 6490; S. Halazy, A. Ehrhard, A. Eggenspiller, V. Bergés-Gross and C. Danzin, Tetrahedron, 1996, 52, 315; D. B. Berkowitz, and D. G. Sloss, J. Org. Chem., 1995, 60, 7047 and references cited therein.
3. T. R. Burke, M. S. Smyth, A. Otaka, M. Nomizu, P. P. Roller, G. Wolf, R. Case and S. E. Shoelson, Biochemistry, 1994, 33, 6490; S. Halazy, A. Ehrhard, A. Eggenspiller, V. Bergés-Gross and C. Danzin, Tetrahedron, 1996, 52, 315; D. B. Berkowitz, and D. G. Sloss, J. Org. Chem., 1995, 60, 7047 and references cited therein.
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6. P. D. Leeson, K. James, I. C. Lennon, N. J. Liverton, S. Aspley and R. G. Jackson, Bioorg. Med. Chem. Lett., 1993, 3, 1925 and references cited therein; A. G. Cole and D. Gani, J. Chem. Soc., Chem. Commun., 1994, 2111; J. Schulz, J. Wilkie, P. Lightfoot, T. Rutherford and D. Gani, J. Chem. Soc., Chem. Commun., 1995, 2353. A Diels-Alder approach using vinylphosphonates has been described leading to analogues in which the phosphorus atom is attached directly to the ring; see C. K. McClure and K. B. Hansen, Tetrahedron Lett., 1996, 37, 2149; C. K. McClure K. J. Herzog and M. D. Bruch, Tetrahedron Lett., 1996, 37, 2153.
7. P. D. Leeson, K. James, I. C. Lennon, N. J. Liverton, S. Aspley and R. G. Jackson, Bioorg. Med. Chem. Lett., 1993, 3, 1925 and references cited therein; A. G. Cole and D. Gani, J. Chem. Soc., Chem. Commun., 1994, 2111; J. Schulz, J. Wilkie, P. Lightfoot, T. Rutherford and D. Gani, J. Chem. Soc., Chem. Commun., 1995, 2353. A Diels-Alder approach using vinylphosphonates has been described leading to analogues in which the phosphorus atom is attached directly to the ring; see C. K. McClure and K. B. Hansen, Tetrahedron Lett., 1996, 37, 2149; C. K. McClure K. J. Herzog and M. D. Bruch, Tetrahedron Lett., 1996, 37, 2153.
8. P. D. Leeson, K. James, I. C. Lennon, N. J. Liverton, S. Aspley and R. G. Jackson, Bioorg. Med. Chem. Lett., 1993, 3, 1925 and references cited therein; A. G. Cole and D. Gani, J. Chem. Soc., Chem. Commun., 1994, 2111; J. Schulz, J. Wilkie, P. Lightfoot, T. Rutherford and D. Gani, J. Chem. Soc., Chem. Commun., 1995, 2353. A Diels-Alder approach using vinylphosphonates has been described leading to analogues in which the phosphorus atom is attached directly to the ring; see C. K. McClure and K. B. Hansen, Tetrahedron Lett., 1996, 37, 2149; C. K. McClure K. J. Herzog and M. D. Bruch, Tetrahedron Lett., 1996, 37, 2153.
9. P. D. Leeson, K. James, I. C. Lennon, N. J. Liverton, S. Aspley and R. G. Jackson, Bioorg. Med. Chem. Lett., 1993, 3, 1925 and references cited therein; A. G. Cole and D. Gani, J. Chem. Soc., Chem. Commun., 1994, 2111; J. Schulz, J. Wilkie, P. Lightfoot, T. Rutherford and D. Gani, J. Chem. Soc., Chem. Commun., 1995, 2353. A Diels-Alder approach using vinylphosphonates has been described leading to analogues in which the phosphorus atom is attached directly to the ring; see C. K. McClure and K. B. Hansen, Tetrahedron Lett., 1996, 37, 2149; C. K. McClure K. J. Herzog and M. D. Bruch, Tetrahedron Lett., 1996, 37, 2153.
10. A. S. Campbell and G. R. J. Thatcher, Tetrahedron Lett., 1991, 32, 1139.
11. The alcohols are too weakly nucleophilic to react under mild base conditions and strong base promotes the migration of phosphorus from carbon to oxygen as described originally by Kondo and co-workers: M. Obayashi, E. Ito, K. Matsui and K. Kondo, Tetrahedron Lett., 1982, 23, 2323.
12. 3 group in a nucleoside analogue has been described; C. Schmit, Synlett, 1994, 241. Motherwell and coworkers have described the addition of phosphityl radicals to difluoroalkenes, another viable approach to the problem described in this communication; T. H. Herpin, J. S. Houlton, W. B. Motherwell, B. P. Roberts and J.-M. Weibel, Chem. Commun., 1996, 613.
13. 3 group in a nucleoside analogue has been described; C. Schmit, Synlett, 1994, 241. Motherwell and coworkers have described the addition of phosphityl radicals to difluoroalkenes, another viable approach to the problem described in this communication; T. H. Herpin, J. S. Houlton, W. B. Motherwell, B. P. Roberts and J.-M. Weibel, Chem. Commun., 1996, 613.
14. Cerium-mediated conjugate additions to nitroalkenes have been achieved; T. Lequeux and J. M. Percy, Synlett, 1995, 361.
15. The synthesis of 2 has been performed on a 20 g scale (77%) following our published procedure: T. Lequeux and J. M. Percy, J. Chem. Soc., Chem. Commun., 1995, 2111.
16. M. W. Rathke and M. Nowak, J. Org. Chem., 1985, 50, 2624.
17. F. Brion, Tetrahedron Lett., 1982, 23, 5299.
18. J. Cossy, J. L. Ranaivosata, V. Bellosta, J. Ancerewicz, R. Ferrito and P. Vogel, J. Org. Chem., 1995, 60, 8351. For a review, see P. Vogel, D. Fattori, F. Gasparini and C. Le Drian, Synlett, 1990, 173.
19. J. Cossy, J. L. Ranaivosata, V. Bellosta, J. Ancerewicz, R. Ferrito and P. Vogel, J. Org. Chem., 1995, 60, 8351. For a review, see P. Vogel, D. Fattori, F. Gasparini and C. Le Drian, Synlett, 1990, 173.