Stereocontrol with phosphine oxides: synthesis of optically active cyclopropyl ketones

Abstract

Treatment of β-keto γ′-hydroxy phosphine oxides, or silylated hemiacetal derivatives of these compounds, with potassium tert-butoxide in tert-butyl alcohol leads to the formation of cyclopropyl ketones. The synthesis of optically active 1,2-di- and 1,2,3-trisubstituted cyclopropyl ketones is described. The reaction is kinetically controlled and the ring-closure is generally stereospecific. A model is described to explain the stereochemical course of the reaction.

References

1. R. M. Williams, G. J. Fegley, R. Gallegos, F. Schaefer and D. L. Pruess, Tetrahedron, 1996, 52, 1149.
2. (a) F. Cluet, A. Haudrechy, P. Le Ber, P. Sinaÿ and A. Wick, Synlett, 1994, 913; (b) R. Csuk and Y. von Scholz, Tetrahedron, 1995, 51, 7193; (c) Z. Zhao, T. Yang, M. Lee, D. Lee, M. G. Newton and C. K. Chu, J. Org. Chem., 1995, 60, 5236; (d) J. Nokami, H. Matsuura, K. Nakasima and S. Shibata, Chem. Lett., 1994, 6, 1071; (e) L. Mévellec and F. Huet, Tetrahedron Lett., 1995, 36, 7441.
3. S. Shuto, S. Ono, Y. Hase, N. Kamiyama and A. Matsuda, Tetrahedron Lett., 1996, 37, 641.
4. (a) A. Hercouet, B. Bessires and M. Le Corre, Tetrahedron: Asymmetry, 1996, 7, 1267; (b) K. Shimamoto, M. Ishida, H. Shinozaki and Y. Ohfune, J. Org. Chem, 1991, 56, 4167; (c) K. Burgess and W. Li, Tetrahedron Lett., 1995, 36, 2725.
5. C. H. Stammer, Tetrahedron, 1990, 46, 2231.
6. E. J. Corey and T. G. Gant, Tetrahedron Lett., 1994, 35, 5373.
7. T. Fakuda and T. Katsuki, Synlett, 1995, 825.
8. (a) K. Ito and T. Katsuki, Synlett, 1993, 638; (b) D. Müller, G. Umbrict, B. Weber and A. Pfaltz, Helv. Chim. Acta, 1991, 74, 232; (c) M. P. Doyle, B. D. Brandes, A. P. Kazala, R. J. Pieters, M. B. Jarstfer, L. M. Watkins and C. T. Eagle, Tetrahedron Lett., 1990, 31, 6613.
9. (a) R. E. Lowenthal and S. Masamune, Tetrahedron Lett., 1991, 32, 7373; (b) S. Kanemasa, S. Hamura, E. Harada and H. Yamamoto, Tetrahedron Lett., 1994, 35, 7985; (c) H. Nishiyama, Y. Itoh, H. Matsumoto, S.-B. Park and K. Itoh, J. Am. Chem. Soc., 1994, 116, 2223; (d) R. E. Lowenthal, A. Abiko and S. Masamune, Tetrahedron Lett., 1990, 31, 6005; (e) D. A. Evans, K. A. Woepel, M. M. Hinman and M. M. Faul, J. Am. Chem. Soc., 1991, 113, 726.
10. (a) S. F. Martin, C. J. Oalman and S. Liras, Tetrahedron Lett., 1992, 33, 6727; (b) M. P. Doyle, R. J. Dieters, S. F. Martin, R. E. Austin, C. J. Oalmann and P. Müller, J. Am. Chem. Soc., 1991, 113, 1423; (c) M. P. Doyle, M. Y. Eismont, M. N. Protopopova and M. M. Y. Kwan, Tetrahedron, 1994, 50, 1665.
11. (a) A. B. Charette and H. Juteau, J. Am. Chem. Soc., 1994, 116, 2651; (b) Y. Ukaji, M. Nishimura and T. Fujisawa, Chem. Lett., 1992, 61.
12. For example, see: A. G. M. Barrett, W. W. Doubleday, K. Kasdorf and G. J. Tustin, J. Org. Chem., 1996, 61, 3280.
13. A. G. M. Barrett and K. Kasdorf, Chem. Commun., 1996, 325.
14. M. Yoshida, M. Ezaki, M. Hashimoto, M. Yamashiti, N. Shigematsu, M. Okuhara, M. Kohsaka and K. Horikoshi, J. Antibiot., 1990, 7, 748.
15. C. R. Johnson and C. W. Schroeck, J. Am. Chem. Soc., 1971, 93, 5303.
16. S. Hanessian, D. Andreotti and A. Gomtsyan, J. Am. Chem. Soc., 1995, 117, 10393.
17. P. Wallace and S. Warren, J. Chem. Soc., Perkin Trans. 1, 1988, 2971.
18. N. A. Portnoy, K. S. Yong and A. H. Aguiar, Tetrahedron Lett., 1971, 2559.
19. (a) L. Horner, H. Homann and V. G. Toscano, Chem. Ber., 1962, 95, 536; (b) R. A. Izydore and R. G. Ghirardelli, J. Org. Chem., 1973, 38, 1790.
20. E. E. Schweizer and W. S. Creasy, J. Org. Chem., 1971, 36, 2379.
21. (a) Preliminary communication: A. Nelson and S. Warren, Tetrahedron Lett., 1996, 37, 1501; (b) N. Feeder, G. Hutton, A. Nelson and S. Warren, J. Chem. Soc., Perkin Trans. 1, 1999, preceding paper.
22. (a) H. C. Kolb, M. S. VanNieuwenhze and K. B. Sharpless, Chem. Rev., 1994, 94, 2483; (b) K. B. Sharpless, W. Amberg, Y. L. Bennani, G. A. Crispino, J. Hartung, K.-S. Jeong, H.-L. Kwong, K. Morikawa, Z.-M. Wang, D. Xu and X.-L. Zhang, J. Org. Chem., 1992, 57, 2768.
23. H. C. Kolb and K. B. Sharpless, Tetrahedron, 1992, 48, 10515.
24. A. Nelson and S. Warren, J. Chem. Soc., Perkin Trans. 1, 1999, 1963.
25. (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.
26. (a) H. C. Kolb, P. G. Andersson and K. B. Sharpless, J. Am. Chem. Soc., 1994, 116, 1278; (b) P.-O. Norrby, H. C. Kolb and K. B. Sharpless, J. Am. Chem. Soc., 1994, 116, 8470.
27. E. J. Corey and M. Chaykovsky, J. Am. Chem. Soc., 1962, 84, 867.
28. L. Dechoux and E. Doris, Tetrahedron Lett., 1994, 35, 2017.
29. N. J. Barnes, A. H. Davidson, L. R. Hughes, G. Procter and V. Rajcoomar, Tetrahedron Lett., 1981, 22, 1751.
30. (a) J. A. Dale, D. L. Dull and H. S. Mosher, J. Org. Chem., 1969, 34, 2543; (b) Y. Goldberg and H. Alper, J. Org. Chem., 1992, 57, 3731; (c) D. E. Ward and C. K. Rhee, Tetrahedron Lett., 1991, 32, 7165.
31. K. Mislow and J. Siegel, J. Am. Chem. Soc., 1984, 106, 3319.
32. F. X. Wilson, G. W. J. Fleet, K. Vogt, Y. Wang, D. R. Witty, S. Choi, R. Storer, P. L. Meyers and C. J. Wallis, Tetrahedron Lett., 1990, 31, 6931.
33. Veibel, Biochem. Z., 1931, 239, 457.
34. A. M. d'A. R. Gonsalves, R. A. W. Johnstone, M. M. Pereira and J. Shaw, J. Chem. Soc., Perkin Trans. 1, 1991, 645.