Lewis acid promoted aziridination of imines with semistabilized sulfonium ylides: highly stereoselective synthesis of vinyl- and ethynyl-aziridines

Abstract

cis-Vinyl- and cis-ethynyl-aziridines are furnished in high yields and high stereoselectivity by aziridination of unactivated N-aryl or N-alkyl imines with S-ylides in the presence of Lewis acids.

References

1. (a) K. B. Hansen, N. S. Finney and E. N. Jacobsen, Angew. Chem., Int. Ed. Engl., 1995, 34, 676; (b) K. G. Rasmussen and K. A. Jørgensen, J. Chem. Soc., Chem. Commun., 1995, 1401; (c) Z. Zhu and J. H. Espenson, J. Org. Chem., 1995, 60, 7090.
2. For leading references see (a) V. K. Aggarwal, A. Thompson, R. V. H. Jones and M. C. H. Standen, J. Org. Chem., 1996, 61, 8368; (b) A.-H. Li, L.-X. Dai and X.-L. Hou, Chem. Commun., 1996, 491; (c) A.-H. Li, L.-X. Dai and X.-L. Hou, J. Chem. Soc., Perkin Trans. 1, 1996, 867; (d) A.-H. Li, L.-X. Dai, X.-L. Hou and M.-B. Chen, J. Org. Chem., 1996, 61, 4641; (e) A.-H. Li, L.-X. Dai and X.-L. Hou, J. Chem. Soc., Perkin Trans. 1, 1996, 2725.
3. 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. Jecobsen, J. Am. Chem. Soc., 1993, 115, 5326; P. Müller, C. Baud and Y. Jacquier, Tetrahedron, 1996, 52, 1543.
4. X.-L. Hou, X.-F. Yang and L.-X. Dai, to be published.
5. Some methods for desulfonylation for nitrogen atom: T. Fukuyama, C.-K. Jow and M. Cheung, Tetrahedron Lett., 1995, 36, 6373; E. Vedejs and S. Lin, J. Org. Chem., 1994, 59, 1602; K. Bellos, H. Stamm and D. Speth, J. Org. Chem., 1991, 56, 6846; R. C. Roemmele and H. Rapoport, J. Org. Chem., 1988, 53, 2367 and references cited therein.
6. (a) B. E. Love, P. S. Raje and T. C. Williams II, Synlett, 1994, 493; (b) G. I. Georg, G. C. B. Harriman and S. A. Peterson, J. Org. Chem., 1995, 60, 7366; (c) W. B. Jennings and C. J. Lovely, Tetrahedron, 1991, 47, 5561; (d) S. M. Weinreb, D. M. Demko and T. A. Lessen, Tetrahedron Lett., 1986, 27, 2099.
7. G. E. Keck and E. J. Enholm, J. Org. Chem., 1985, 50, 146; D.-K. Wang, L.-X. Dai and X.-L. Hou, Tetrahedron Lett., 1995, 36, 8649.
8. For example, the Lewis acid is necessary in the synthesis of aziridines from imines and ethyl diazoacetate, see L. Casarrubios, J. A. Pérez, M. Brookhart and J. L. Templeton, J. Org. Chem., 1996, 61, 8358.
9. For the preparation of 3-trimethylsilylallyldiphenylsulfonium perchlorate 2m and 3-trimethylsilyprop-2-ynyldiphenlsulfoniun perchlorate 2n, see T. K. Jones and S. E. Denmark, Org. Synth., 1990, Coll. Vol. 7, 524; R. W. LaRochelle, B. M. Trost and L. Krepski, J. Org. Chem., 1971, 36, 1126.
10. N. Mimura, T. Ibuka, M. Akaji, Y. Miwa, T. Taga, K. Nakai, H. Tamamura, N. Fujii and Y. Yamamoto, Chem. Commun., 1996, 351 The cis-selectivity phenomenon were also found M. Komatsu, M. Ohno, S. Tsuno and Y. Ohshiro, Chem. Lett., 1990, 575 The Darzens fashion G. Cainelli, M. Panurizio and D. Giacomini, Tetrahedron Lett., 1991, 121.