Diastereoselective nucleophilic additions to vinyl phosphine oxides

Abstract

Some hydrogen, carbon, silicon, sulfur, nitrogen and oxygen nucleophiles react diastereoselectively with γ-oxygenated chiral vinyl phosphine oxides to give β-substituted phosphine oxides. Lithium N-benzyl-α-methylbenzylamide adds to prochiral vinyl phosphine oxides in the presence of trimethylsilyl chloride to provide, after protodesilylation, β-amino phosphine oxides as single diastereoisomers.

References

1. J. Clayden and S. Warren, Angew. Chem., Int. Ed. Engl., 1996, 35, 241.
2. D. Cavalla, W. B. Cruse and S. Warren, J. Chem. Soc., Perkin Trans. 1, 1987, 1883.
3. D. Hall, A.-F. Sévin and S. Warren, Tetrahedron Lett., 1991, 32, 7123.
4. J. Clayden, E. W. Collington, R. B. Lamont and S. Warren, Tetrahedron Lett., 1993, 34, 2203.
5. C. Guéguen, P. O'Brien, S. Warren and P. Wyatt, J. Organomet. Chem., 1997, 529, 279.
6. A. Nelson and S. Warren, Tetrahedron Lett., 1996, 37, 1501.
7. (a) T. Minami and J. Motoyoshiya, Synthesis, 1992, 333; (b) I. C. Baldwin, R. P. Beckett and J. M. J. Williams, Synthesis, 1996, 34.
8. D. J. Collins, S.-A. Mollard, N. Rose and J. M. Swann, Aust. J. Chem., 1974, 27, 2365.
9. K. M. Pietrusiewicz, M. Zablocka and J. Monkiewicz, J. Org. Chem., 1984, 49, 1522.
10. I. Fleming, S. Gil, A. K. Sarkar and T. Schmidlin, J. Chem. Soc., Perkin Trans. 1, 1992, 3351.
11. (a) A. Brandi, P. Cannarò, K. M. Pietrusiewicz, M. Zablocka and M. Wieczorek, J. Org. Chem., 1989, 54, 3073; (b) A. Brandi, S. Cicchi, A. Goti and K. M. Pietrusiewicz, Gazz. Chim. Ital., 1991, 121, 285.
12. C. Santelli-Rouvier, Synthesis, 1988, 64.
13. D. H. Williams and I. Fleming, Spectroscopic methods in organic chemistry, 5th edn., McGraw-Hill, London, 1995, p. 168.
14. Y. L. Bennani and K. B. Sharpless, Tetrahedron Lett., 1993, 34, 2083.
15. (a) A. Nelson, P. O'Brien and S. Warren, Tetrahedron Lett., 1995, 36, 2685; (b) A. Nelson and S. Warren, J. Chem. Soc., Perkin Trans. 1, 1997, 2645.
16. J. Clayden and S. Warren, J. Chem. Soc., Perkin Trans. 1, 1994, 2811.
17. P. O'Brien and S. Warren, Tetrahedron: Asymmetry, 1996, 7, 3431.
18. Preliminary communication: J. Clayden, A. Nelson and S. Warren, Tetrahedron Lett., 1997, 38, 3471.
19. (a) P. M. Ayrey, M. A. Bolton, A. D. Buss, N. Greeves, D. Levin, P. Wallace and S. Warren, J. Chem. Soc., Perkin Trans. 1, 1992, 3407; (b) P. Wallace and S. Warren, J. Chem Soc., Perkin Trans. 1, 1992, 3169.
20. K. Okuma, Y. Tanaka, H. Ohta and H. Matsuyama, Bull. Chem. Soc. Jpn., 1993, 66, 2623.
21. E. Domínguez and J. C. Carretero, Tetrahedron Lett., 1993, 34, 5803.
22. N. Feeder, G. Hutton and S. Warren, Tetrahedron Lett., 1994, 35, 5911.
23. (a) E. J. Corey and A. W. Gross, Tetrahedron Lett., 1984, 25, 495; (b) C. Guéguen, P. O'Brien, S. Warren and P. Wyatt, J. Organomet Chem., 1997, 529, 279.
24. (a) D. J. Ager and I. Fleming, J. Chem. Soc., Chem. Commun., 1978, 177; (b) D. J. Ager, I. Fleming and S. K. Patel, J. Chem. Soc., Perkin Trans. 1, 1981, 2520.
25. I. Fleming, in Organocopper Reagents, ed. R. J. K. Taylor, Oxford University Press, Oxford, 1994, p. 256.
26. D. J. Ager, “The Peterson OleWnation Reaction”, in Organic Reactions, ed. L. A. Paquette, 1990, vol. 38, p. 1.
27. (a) Y. Yamamoto, Y. Chounan, S. Nishii, T. Ibuka and H. Kitahara, J. Am. Chem. Soc., 1992, 114, 7652; (b) T. Ibuka and Y. Yamamoto, Synlett, 1992, 769.
28. M. Hirama, H. Hioki, S. Itô and C. Kabuto, Tetrahedron Lett., 1988, 29, 3121.
29. R. F. W. Jackson, S. P. Standen and W. Clegg, Tetrahedron Lett., 1991, 32, 5393.
30. J. Leonard, Contemp. Org. Synth., 1994, 387.
31. S. G. Davies and T. D. McCarthy, Synlett, 1995, 700.
32. (a) E. Juaristi, P. Murer and D. Seebach, Synthesis, 1993, 1243; (b) C. M. Cain, R. P. C. Cousins, G. Coumbarides and N. S. Simpkins, Tetrahedron, 1990, 46, 523.
33. Preliminary communication: B. Bartels, C. Gonzalez Martín, A. Nelson, M. G. Russell and S. Warren, Tetrahedron Lett., 1998, 39, 1637.
34. J. Medlock and S. Warren, unpublished observations.
35. J. Barluenga, R. Sanz and F. J. Fañanás, Tetrahedron Lett., 1997, 38, 2763.
36. B. H. Lipshutz, M. R. Wood and C. W. Lindsley, Tetrahedron Lett., 1995, 36, 4385.
37. J. F. Costello, S. G. Davies and O. Ichihara, Tetrahedron: Asymmetry, 1994, 5, 1999.
38. J. E. Davies, R. P. Davies, L. Dunbar, P. R. Raithby, M. G. Russell, R. Snaith and S. Warren, Angew. Chem., Int. Ed. Engl., 1997, 36, 2334.
39. (a) T. Hayashi, M. Konishi, M. Fukushima, K. Kanehira, T. Hioki and M. Kumada, J. Org. Chem., 1983, 48, 2195; (b) T. Hayashi, M. Fukushima, M. Konishi and M. Kumada, Tetrahedron Lett., 1980, 21, 79.
40. I. W. Davies, T. Gallagher, R. B. Lamont and D. I. C. Scopes, J. Chem. Soc., Chem. Commun., 1992, 335.
41. W. C. Still, M. Kahn and A. Mitra, J. Org. Chem., 1978, 43, 2923.
42. J. B. Baudin, G. Hareau, S. A. Julia, R. Lorne and O. Ruel, Bull. Soc. Chim Fr., 1993, 130, 856.
43. E. E. Aboujaoude and N. Collignon, Synth. Commun., 1987, 17, 1559.