Hetero-Diels–Alder reactions of α-carbonylated styrylphosphonates with enol ethers. High-pressure influence on reactivity and diastereoselectivity

Abstract

Variously substituted α-carbonylated styrylphosphonates 5 were easily prepared by Knoevenagel-type syntheses, and used as oxadienes in hetero-Diels–Alder [4 + 2] cycloadditions with enol ethers, to give new phosphonylated 3,4-dihydro-2H-pyrans 6. It was confirmed that the reactivity , as well as the trans-diastereoselectivity of the reaction, was significantly enhanced by the use of high-pressure conditions, particularly in the presence of Bu^tOH as a co-solvent. Moreover, a one-pot synthesis of 6 via a tandem-sequence Knoevenagel and hetero-Diels–Alder reactions was achieved.

References

1. L. F. Tietze and G. Kettschau, Top. Curr. Chem., 1997, 189, 1.
2. L. F. Tietze, G. Kettschau, J. A. Gewert and A. Schuenhauer, Curr. Org. Chem., 1998, 2, 19.
3. A. Ichihara and Oikawa, Curr. Org. Chem., 1998, 2, 365.
4. K. N. Houk, J. Am. Chem. Soc., 1973, 95, 4092.
5. L. A. Telan, C.-D. Poon and S. A. Evans, Jr., J. Org. Chem., 1996, 61, 7455.
6. D. A. Evans and J. S. Johnson, J. Am. Chem. Soc., 1998, 120, 4895.
7. H. Al-Badri, E. About-Jaudet and N. Collignon, Synthesis, 1994, 1072.
8. H. Al-Badri, E. About-Jaudet, J.-C. Combret and N. Collignon, Synthesis, 1995, 1401.
9. H. Al-Badri, E. About-Jaudet and N. Collignon, J. Chem. Soc., Perkin Trans. 1, 1996, 931.
10. F. Chevalier, H. Al-Badri and N. Collignon, Bull. Soc. Chim. Fr., 1997, 134, 801.
11. H. Al-Badri, E. About-Jaudet and N. Collignon, Tetrahedron Lett., 1996, 37, 2951.
12. E. Aboujaoude, N. Collignon and P. Savignac, J. Organomet. Chem., 1984, 264, 9.
13. A. N. Pudovik, G. E. Yasterbova and V. I. Nikitina, J. Gen. Chem. USSR (Engl. Transl.), 1967, 37, 480.
14. R. Sakoda, H. Matsumoto and K. Seto, Synthesis, 1993, 705.
15. G. L. Kenyon and F. H. Westheimer, J. Am. Chem. Soc., 1966, 88, 3557.
16. C. Benezra, S. Niec and G. Ourisson, Bull. Soc. Chim. Fr., 1967, 1140.
17. M. J. Cook and G. Desimoni, Tetrahedron, 1971, 27, 257.
18. S. S. Hall, G. F. Weber and A. Duggan, J. Org. Chem., 1978, 43, 667.
19. M. Maier and R. R. Schmidt, Liebigs Ann. Chem., 1985, 2261.
20. K. Matsumoto and A. Sera, Synthesis, 1985, 999.
21. G. Jenner, Tetrahedron, 1997, 53, 2669.
22. L. F. Tietze, M. Henrich, A. Niklaus and M. Buback, Chem. Eur. J., 1999, 5, 297.
23. J. M. Mellor and C. F. Webb, J. Chem. Soc., Perkin Trans. 2, 1974, 17.
24. D. L. Boger and K. D. Robarge, J. Org. Chem., 1988, 53, 3373.
25. G. Dujardin, M. Maudet and E. Brown, Tetrahedron Lett., 1997, 38, 1555.
26. J. Thorhauge, M. Johannsen and K. A. Jorgensen, Angew. Chem., Int. Ed., 1998, 37, 2404.
27. D. A. Evans, E. J. Olhava, J. S. Johnson and J. M. Janey, Angew. Chem., Int. Ed., 1998, 37, 3372.
28. B. B. Snider and Q. Zhang, J. Org. Chem., 1991, 56, 4908.
29. L. F. Tietze, C. Schneider and A. Grote, Chem. Eur. J., 1996, 2, 139.
30. L. F. Tietze and U. Beifuss, Angew. Chem., Int. Ed. Engl., 1993, 32, 131.
31. L. F. Tietze, J. Heterocycl. Chem., 1990, 27, 47.