Enantioselective synthesis of epoxides and aziridines by asymmetric methylidene transfer from a sulfimide to carbonyl compounds and imines

Abstract

The sodium salt of sulfimide 2 is a useful asymmetric methylidene transfer agent for the synthesis of enantiomerically enriched epoxides and aziridines. Moderate enantioselectivities are observed with a broad range of carbonyl compounds and with imines. An enantiomerically enriched β-adrenoreceptor agonist analogue was prepared using the new method.

References

1. Asymmetric epoxidations: R. A. Johnson and K. B. Sharpless, in Catalytic Asymmetric Synthesis, ed. I. Ojima, VCH, Weinheim, 1993, Section 4.1; E. N. Jacobsen, in Catalytic Asymmetric Synthesis, ed. I. Ojima, VCH, Weinheim, 1993, Section 4.2.
2. Asymmetric aziridinations: D. A. Evans, M. M. Faul, M. T. Bilodeau, B. A. Anderson and D. M. Barnes, J. Am. Chem. Soc., 1993, 115, 5328; Z. Li, K. R. Conser and E. N. Jacobsen, J. Am. Chem. Soc., 1993, 115, 5326; P. Müller, C. Baud and Y. Jacquier, Tetrahedron, 1996, 52, 1543; M. J. Södergren, D. A. Alonso and P. G. Andersson, Tetrahedron: Asymmetry, 1997, 8, 3563.
3. S. E. Kelly, in Comprehensive Organic Synthesis, ed. B. M. Trost and I. Fleming, Pergamon, Oxford, 1991, Section 3.1.
4. A.-H. Li, L.-X. Dai and V. K. Aggarwal, Chem. Rev., 1997, 97, 2341.
5. M. Tokunaga, J. F. Larrow, F. Kakiuchi and E. N. Jacobsen, Science, 1997, 277, 936.
6. A. Solladié-Cavallo and A. Diep-Vohuule, J. Org. Chem., 1995, 60, 3494.
7. B. M. Trost and R. F. Hammen, J. Am. Chem. Soc., 1973, 95, 962.
8. C. R. Johnson, R. A. Kirchoff, R. J. Reischer and G. F. Katekar, J. Am. Chem. Soc., 1973, 95, 4287 There is an error in the structure labelled as 4-(R) in this paper since the molecule shown is of (S) configuration.
9. S. S. Taj, A. C. Shah, D. Lee, G. Newton and R. Soman, Tetrahedron: Asymmetry, 1995, 6, 1731; S. S. Taj and R. Soman, Tetrahedron: Asymmetry, 1994, 5, 1513.
10. C. P. Baird and P. C. Taylor, J. Chem. Soc., Chem. Commun., 1995, 893.
11. V. K. Aggarwal, A. Thompson, R. V. H. Jones and M. C. H. Standen, J. Org. Chem., 1996, 61, 8368.
12. A.-H. Li, Y.-G. Zhou, L.-X. Dai, X.-L. Hou, L.-J. Xia and L. Lin, Angew. Chem., Int. Ed. Engl., 1997, 36, 1317.
13. D. J. Cram, J. Day, D. R. Rayner, D. M. von Schrilz, D. J. Duchamp and D. C. Garwood, J. Am. Chem. Soc., 1970, 92, 7369.
14. G. Celentano, S. Colonna, N. Gaggero and C. Richelmi, Chem. Commun., 1998, 701.
15. L. A. Bigelow and H. Eatough, Org. Synth., 1941, 1, 80; W. B. Jennings and C. J. Lovely, Tetrahedron Lett., 1988, 29, 3725.
16. (a) Y. Tamura, H. Matsushima and M. Ikeda, Synthesis, 1976, 35; (b) Y. Tamura, S. M. Bayomi, K. Sumoto and M. Ikeda, Synthesis, 1977, 693; (c) C. R. Johnson, K. Mori and A. Nakanishi, J. Org. Chem., 1979, 2065.
17. A. J. Pearson, S. L. Blystone, H. Nar, A. A. Pinkerton, B. A. Roden and J. Y. Yoon, J. Am. Chem. Soc., 1989, 111, 134.
18. A. Solladié-Cavallo and M. Bencheqroun, J. Org. Chem., 1992, 57, 5831 we used a modified procedure described by the same group in Solladié-Cavallo, ref. 6 above.
19. S. K. Taylor, G. H. Hockerman, G. L. Karrick, S. B. Lyle and S. B. Schramm, J. Org. Chem., 1983, 48, 2449.
20. N. Krause and D. Seebach, Chem. Ber., 1988, 121, 1315.
21. M. Alvarez, R. Granados, R. Lavilla and M. Salas, J. Heterocycl. Chem., 1985, 22, 745.
22. E. Liepins, V. A. Pestunovich, A. V. Eremeev, D. A. Tikhomirov and N. P. Gaidarova, Khim. Geterotsikl. Soedin., 1977, 906 (Chem. Abstr., 1977, 87, 183795b).
23. US 3281468 (Chem. Abstr., 1967, 67, 11329y).