Control of stereochemistry with phosphine oxides: asymmetric synthesis of 4-alkenyloxazolidin-2-ones with 1,4-related stereogenic centres across a double bond

Abstract

Treatment of optically active epoxyurethanes with four contiguous stereogenic centres [derived from a kinetic resolution during Sharpless epoxidation of diphenylphosphinoyl (Ph₂PO) allylic alcohols] with base leads to sequential regioselective intramolecular nucleophilic attack (on the epoxide) and Horner–Wittig elimination to give single geometrical isomers of alkenyl oxazolidinones. Any stereoisomer of 4-alkenyloxazolidin-2-ones containing 1,4-related stereogenic centres spanning a double bond of either geometry can be produced with control over geometrical (E,Z ), relative (syn,anti ) and absolute (R,S ) stereochemistry.

References

1. J. Clayden and S. Warren, Angew. Chem., Int. Ed. Engl., 1996, 35, 241.
2. M. G. Finn and K. B. Sharpless in Asymmetric Synthesis, Academic Press, Orlando( 1985), ed. J. D. Morrison, vol. 5, ch. 8; Y. Gao, R. M. Hanson, J. M. Klunder, S. Y. Ko, H. Masamune and K. B. Sharpless, J. Am. Chem. Soc., 1987, 109, 5765.
3. A. Nelson and S. Warren, Tetrahedron Lett., 1996, 37, 1501.
4. J. Clayden, A. B. McElroy and S. Warren, J. Chem. Soc., Perkin Trans. 1, 1995, 1913.
5. Preliminary communication: J. Clayden, E. W. Collington, R. B. Lamont and S. Warren, Tetrahedron Lett., 1993, 34, 2203.
6. J. Clayden and S. Warren, J. Chem. Soc., Perkin Trans. 1, 1993, 2913; J. Clayden and S. Warren, J. Chem. Soc., Perkin Trans. 1, 1994, 1529.
7. J. Clayden and S. Warren, J. Chem. Soc., Perkin Trans. 1, 1994, 2811.
8. J. Clayden, E. Egert, A. B. McElroy and S. Warren, J. Chem. Soc., Perkin Trans. 1, 1994, 2801.
9. W. R. Roush and M. A. Adam, J. Org. Chem., 1985, 50, 3752.
10. N. Minami, S. S. Ko and Y. Kishi, J. Am. Chem. Soc., 1982, 104, 1109.
11. V. Jäger, U. Stahl and W. Hümmer, Synthesis, 1991, 776; J. C. Schmidhauser and K. L. Longley, Tetrahedron Lett., 1991, 32, 7155.
12. T. W. Hart and B. Vacher, Tetrahedron Lett., 1992, 33, 3009.
13. S. W. McCombie, B. B. Shankar and A. K. Ganguly, Tetrahedron Lett., 1985, 26, 6301.
14. S. W. McCombie and W. A. Metz, Tetrahedron Lett., 1987, 28, 383.
15. W. R. Roush, R. J. Brown and M. DiMare, J. Org. Chem., 1983, 48, 5083.
16. E. J. Corey, P. B. Hopkins, J. E. Munroe, A. Marfat and S.-I. Hashimoto, J. Am. Chem. Soc., 1980, 102, 7987.
17. A. D. Buss, W. B. Cruse, O. Kennard and S. Warren, J. Chem. Soc., Perkin Trans. 1, 1984, 243.
18. D. Xu and K. B. Sharpless, Tetrahedron Lett., 1993, 34, 951; M. P. Sibi and P. A. Renhowe, Tetrahedron Lett., 1990, 31, 7407; M. P. Sibi and B. Li, Tetrahedron Lett., 1992, 33, 4115; P. L. Beaulieu, J.-L. Duceppe and C. Johnson, J. Org. Chem., 1991, 56, 4196.
19. T. Ibuka, H. Habashita, S. Funakoshi, N. Fujii, Y. Oguchi, T. Uyehara and Y. Yamamoto, Angew. Chem., Int. Ed. Engl., 1990, 29, 801.
20. T. Ibuka, K. Nakai, H. Habashita, Y. Hotta, N. Fujii, N. Mimura, Y. Miwa, T. Taga and Y. Yamamoto, Angew. Chem., Int. Ed. Engl., 1994, 33, 652 and references therein.
21. A. C. Bohrstedt, J. V. N. V. Prasad and D. Rich, Tetrahedron Lett., 1993, 34, 5217.
22. P. J. Murphy and G. Procter, Tetrahedron Lett., 1990, 31, 1059.
23. D. Hall, A.-F. Sévin and S. Warren, Tetrahedron Lett., 1991, 32, 7123.
24. See, for example, V. K. Aggarwal, I. Coldham, S. McIntyre and S. Warren, J. Chem. Soc., Perkin Trans. 1, 1991, 451; R. C. Hartley, I. C. Richards and S. Warren, J. Chem. Soc., Perkin Trans. 1, 1994, 508.
25. For an exception, see M. A. M. Fuhry, A. B. Holmes and D. R. Marshall, J. Chem. Soc., Perkin Trans. 1, 1993, 2743.
26. H. J. Mitchell and S. Warren, Tetrahedron Lett., 1996, 37, 2105.
27. W. C. Still, M. Kahn and A. Mitra, J. Org. Chem., 1978, 43, 2923.