A 2,3-cis-selective synthesis of aziridines bearing a vinyl group from allyl methyl carbonates and allyl mesylates

Abstract

A convenient method for the synthesis of synthetically useful chiral 2-vinylaziridines from natural α-amino acids is described. Satisfactory 2,3-cis-selectivities are obtained by exposure of methyl carbonates of various allylic alcohols bearing an N-protected amino group to a catalytic amount of tetrakis(triphenylphosphine)palladium(>0>), Pd(PPh₃)₄, in aprotic solvents such as THF. Base-promoted aziridination of mesylates of various N-protected amino allylic alcohols followed by Pd(PPh₃)₄ catalyzed isomerization for the 2,3-cis-selective synthesis of vinylaziridines is also presented.

References

1. E. J. Moran, J. E. Tellew, Z. Zhao and R. W. Armstrong, J. Org. Chem., 1993, 58, 7848.
2. (a) G. W. Spears, K. Nakanishi and Y. Ohfune, Synlett, 1991, 91; (b) D. Tanner and P. Somfai, Bioorg. Med. Chem. Lett., 1993, 3, 2415; (c) for a review of cyclization reactions of amino allylic alcohols, see Y. Hirai and H. Yokoyama, J. Synth. Org. Chem. Jpn., 1998, 56, 50.
3. F. A. Davis, G. V. Reddy and H. Liu, J. Am. Chem. Soc., 1995, 117, 3651.
4. (a) J. Åhman, T. Jarevång and P. Somfai, J. Org. Chem., 1996, 61, 8148; (b) J. Åhman and P. Somfai, J. Am. Chem. Soc., 1994, 116, 9781; (c) J. Åhman and P. Somfai, Tetrahedron Lett., 1996, 37, 2495.
5. J. Åhman and P. Somfai, Tetrahedron Lett., 1995, 36, 303; J. Åhman and P. Somfai, Tetrahedron, 1995, 51, 9747.
6. T. Hudlicky, J. O. Frazier, G. Seoane, M. Tiedje, A. Seoane, L. D. Kwart and C. Beal, J. Am. Chem. Soc., 1986, 108, 3755; T. Hudlicky, G. Seoane and T. C. Lovelace, J. Org. Chem., 1988, 53, 2094; T. Hudlicky, H. Luna, J. D. Price and F. Rulin, J. Org. Chem., 1990, 55, 4683; W. H. Pearson, S. C. Bergmeier, S. Degan, K.-C. Lin, Y.-F. Poon, J. M. Schkeryantz and J. P. Williams, J. Org. Chem., 1990, 55, 5719.
7. (a) J. Åhman, P. Somfai and D. Tanner, J. Chem. Soc., Chem. Commun., 1994, 2785; (b) P. Somfai and J. Åhman, Tetrahedron Lett., 1995, 36, 1953.
8. (a) A. A. Cantrill, A. N. Jarvis, H. M. I. Osborn, A. Ouadi and J. B. Sweeney, Synlett, 1996, 847; (b) H. Aoyama, N. Mimura, H. Ohno, K. Ishii, A. Toda, H. Tamamura, A. Otaka, N. Fujii and T. Ibuka, Tetrahedron Lett., 1997, 38, 7383.
9. F. A. Davis and G. V. Reddy, Tetrahedron Lett., 1996, 37, 4349.
10. U. M. Lindström and P. Somfai, J. Am. Chem. Soc., 1997, 119, 8385.
11. (a) 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; (b) P. Wipf and P. C. Fritch, J. Org. Chem., 1994, 59, 4875; (c) N. Fujii, K. Nakai, H. Tamamura, A. Otaka, N. Mimura, Y. Miwa, T. Taga, Y. Yamamoto and T. Ibuka, J. Chem. Soc., Perkin Trans. 1, 1995, 1359; (d) A. Satake, I. Shimizu and Y. Yamamoto, Synlett, 1995, 64; (e) P. Wipf and T. C. Henninger, J. Org. Chem., 1997, 62, 1586.
12. (a) T. Ibuka, H. Habashita, S. Funakoshi, N. Fujii, Y. Oguchi, T. Uyehara and Y. Yamamoto, Angew. Chem., Int. Ed. Engl., 1990, 29, 801; (b) T. Ibuka, H. Habashita, A. Otaka, N. Fujii, Y. Oguchi, T. Uyehara and Y. Yamamoto, J. Org. Chem., 1991, 56, 4370; (c) T. Ibuka, T. Taga, H. Habashita, K. Nakai, H. Tamamura, N. Fujii, Y. Chounan, H. Nemoto and Y. Yamamoto, J. Org. Chem., 1993, 58, 1207; (d) D. Gryko, Z. Urbanczyk-Lipkowska and J. Jurczak, Tetrahedron: Asymmetry, 1997, 8, 4059.
13. (a) G. J. Hanson and T. Lindberg, J. Org. Chem., 1985, 50, 5399; (b) S. Thaisrivongs, D. T. Pals, L. T. Kroll, S. R. Turner and F.-S. Han, J. Med. Chem., 1987, 30, 976; (c) P. G. M. Wuts, S. R. Putt and A. R. Ritter, J. Org. Chem., 1988, 53, 4503; (d) W. J. hompson, T. J. Tucker, J. E. Schwering and J. L. Barnes, Tetrahedron Lett., 1990, 31, 6819; (e) D. J. Kempf, X. C. Wang and S. G. Spanton, Int. J. Pept. Protein Res., 1991, 38, 237; (f) B. E. Green, X. Chen, D. W. Norbeck and D. J. Kempf, Synlett, 1995, 613.
14. Y.-K. Shue, G. M. Carrera, Jr. and A. M. Nadzan, Tetrahedron Lett., 1987, 28, 3225; Y.-K. Shue, M. D. Tufano and A. M. Nadzan, Tetrahedron Lett., 1988, 29, 4041; Y.-K. Shue, G. M. Carrera, Jr., M. D. Tufano and A. M. Nadzan, J. Org. Chem., 1991, 56, 2107.
15. R. S. Coleman and A. J. Carpenter, Tetrahedron Lett., 1992, 33, 1697.
16. A. Spaltenstein, J. J. Leban, J. J. Huang, K. R. Reinhardt, O. H. Viveros, J. Sigafoos and R. Crouch, Tetrahedron Lett., 1996, 37, 1343.
17. M. Kawai, A. S. Boparai, M. S. Bernatowicz and D. H. Rich, J. Org. Chem., 1983, 48, 1876; L. S. L. de Gaeta, M. Czarniecki and A. Spaltenstein, J. Org. Chem., 1989, 54, 4004 and references cited.
18. (a) M. Wada, R. Doi, R. Hosotani, R. Higashide, T. Ibuka, H. Habashita, K. Nakai, N. Fujii and M. Imamura, Pancreas, 1995, 10, 301; (b) K. Miyasaka, S. Kanai, M. Masuda, T. Ibuka, K. Nakai, N. Fujii and S. Funakoshi, J. Auton. Nerv. Syst., 1997, 63, 179; (c) K. Fujimoto, R. Doi, R. Hosotani, M. Wada, J.-U. Lee, T. Koshiba, T. Ibuka, H. Habashita, K. Nakai, N. Fujii and M. Imamura, Life Sci., 1997, 60, 29.
19. J. Tsuji, I. Shimizu, I. Minami and Y. Ohashi, Tetrahedron Lett., 1982, 23, 4809; J. Tsuji, I. Shimizu, I. Minami, Y. Ohashi, T. Sugiura and K. Takahashi, J. Org. Chem., 1985, 50, 1523.
20. J. Tsuji, Palladium Reagents and Catalysis, Wiley, New York, 1995; J. Tsuji and I. Minami, Acc. Chem. Res., 1987, 20, 140; J. Tsuji, Tetrahedron, 1986, 42, 4361.
21. (a) K. Fugami, Y. Morizawa, K. Oshima and H. Nozaki, Tetrahedron Lett., 1985, 26, 857; (b) N. Mimura, T. Ibuka, M. Akaji, Y. Miwa, T. Taga, K. Nakai, H. Tamamura, N. Fujii and Y. Yamamoto, Chem. Commun., 1996, 351 and 1399; (c) T. Ibuka, N. Mimura, H. Aoyama, M. Akaji, H. Ohno, Y. Miwa, T. Taga, K. Nakai, H. Tamamura, N. Fujii and Y. Yamamoto, J. Org. Chem., 1997, 62, 999; (d) synthesis of activated 2-vinylaziridines from 1,4-amino alcohols has appeared recently, see H. F. Olivo, M. S. Hemenway, A. C. Hartwig and R. Chan, Synlett, 1998, 247.
22. (a) T. Ibuka, M. Akaji, N. Mimura, H. Habashita, K. Nakai, H. Tamamura, N. Fujii and Y. Yamamoto, Tetrahedron Lett., 1996, 37, 2849; (b) T. Ibuka, N. Mimura, H. Ohno, K. Nakai, M. Akaji, H. Habashita, H. Tamamura, Y. Miwa, T. Taga, N. Fujii and Y. Yamamoto, J. Org. Chem., 1997, 62, 2982; (c) H. Ohno, N. Mimura, A. Otaka, H. Tamamura, N. Fujii, T. Ibuka, I. Shimizu, A. Satake and Y. Yamamoto, Tetrahedron, 1997, 53, 12933.
23. R. Ramage and J. Green, Tetrahedron Lett., 1987, 28, 2287; J. Green, O. M. Ogunjobi, R. Ramage and A. S. J. Stewart, Tetrahedron Lett., 1988, 29, 4341.
24. M. Fujino, M. Wakimatsu and C. Kitada, Chem. Pharm. Bull., 1981, 29, 2825.
25. M. J. McKennon, A. I. Meyers, K. Drauz and M. Schwarm, J. Org. Chem., 1993, 58, 3568.
26. M.-C. Fournié-Zaluski, P. Coric, S. Turcaud, L. Bruetschy, E. Luce, F. Noble and B. P. Roques, J. Med. Chem., 1992, 35, 1259; C. Bennion, S. Connolly, N. P. Gensmantel, C. Hallam, C. G. Jackson, W. U. Primrose, G. C. K. Roberts, D. H. Robinson and P. K. Slaich, J. Med. Chem., 1992, 35, 2939.
27. V. J. Hruby and K. W. Ehler, J. Org. Chem., 1970, 35, 1690; H. Sugano and M. Miyoshi, J. Org. Chem., 1976, 41, 2352.
28. P. Coutrot, A. Elgadi and C. Grison, Heterocycles, 1989, 28, 1179; F. A. Davis and P. Zhou, Tetrahedron Lett., 1994, 35, 7525; F. A. Davis, P. Zhou and G. V. Reddy, J. Org. Chem., 1994, 59, 3243; F. E. Ziegler and M. Belema, J. Org. Chem., 1994, 59, 7962.
29. (a) B. M. Trost and T. P. Klun, J. Org. Chem., 1980, 45, 4256; (b) R. W. Hoffmann, Chem. Rev., 1989, 89, 1841; (c) S. D. Kahn, C. F. Pau, A. R. Chamberlin and W. J. Hehre, J. Am. Chem. Soc., 1987, 109, 650.