Regiospecific ring-opening reactions of aziridines bearing an α,β-unsaturated ester group with trifluoroacetic acid or methanesulfonic acid: application to the stereoselective synthesis of (E)-alkene dipeptide isosteres

Abstract

Reaction of N-(2,4,6-trimethylphenylsulfonyl)-γ,δ-cis- or -trans-γ,δ-epimino (E)-α,β-enoates with acids such as TFA or methanesulfonic acid (MSA) affords the stereo- and regio-selective ring-opened products in high yields, and subsequent treatment of resulting δ-aminated γ-mesyloxyα,β-enoates with organocopper reagents yields diastereoisomerically pure (E)-alkene dipeptide isosteres.

References

1. J. S. Kaltenbronn, J. P. Hudspeth, E. A. Lunney, B. M. Michniewicz, E. D. Nicolaides, J. T. Repine, W. H. Roark, M. A. Steir, F. J. Tinney, P. K. W. Woo and A. D. Essenburg, J. Med. Chem., 1990, 33, 838; D. Tourwe, J. Couder, M. Ceusters, D. Meert, T. F. Burks, T. H. Kramer, P. Davis, R. Knapp, H. I. Yamamura, J. E. Leysen and G. van Binst, Int. J. Peptide Protein Res., 1992, 39, 131 for a review of syntheses of (E)-alkene dipeptide isosteres up to May 1992, see T. Ibuka, J. Synth. Org. Chem. Jpn., 1992, 50, 953.
2. M. Wada, R. Doi, R. Hosotani, T. Ibuka, H. Habashita, K. Nakai, N. Fujii and M. Imamura, Pancreas, 1995, 10, 31.
3. T. E. Christos, A. Arvanitis, G. A. Cain, A. L. Johnson, R. S. Pottorf, S. W. Tam and W. K. Schmidt, Bioorg. Med. Chem. Lett., 1993, 3, 1035.
4. T. Ibuka, N. Mimura, H. Ohno, K. Nakai, M. Akaji, H. Habashita, H. Tamamura, Y. Miwa, T. Taga and N. Fujii, J. Org. Chem., 1997, 62, 2982.
5. P. Wipf and P. C. Fritch, J. Org. Chem., 1994, 59, 4875; 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.
6. T. Ibuka, H. Habashita, A. Otaka, N. Fujii, Y. Oguchi, T. Uyehara and Y. Yamamoto, J. Org. Chem., 1991, 56, 4370; M. J. Daly, R. A. Ward, D. F. Thompson and G. Procter, Tetrahedron Lett., 1995, 36, 7545.
7. D. Tanner and P. Somfai, Tetrahedron Lett., 1987, 28, 1211; J. Legters, J. G. H. Willems, L. Thijs and B. Zwanenburg, Recl. Trav. Chim. Pays-Bas, 1992, 111, 59; C. M. Rayner, Synlett, 1997, 11.
8. A. Bongini, G. Cardillo, M. Orena, S. Sandri and C. Tomasini, J. Chem. Soc., Perkin Trans. 1, 1986, 1339; 1986, 1345.
9. D. A. Evans, M. M. Faul, M. T. Bilodeau, B. A. Anderson and D. M. Barnes, J. Am. Chem. Soc., 1993, 115, 5328; I. Coldham, A. J. Collis, R. J. Mould and R. E. Rathmell, J. Chem. Soc., Perkin Trans. 1, 1995, 2739; F. A. Davis and G. V. Reddy, Tetrahedron Lett., 1996, 37, 4349.
10. F. A. Davis and P. Zhou, Tetrahedron Lett., 1994, 35, 7525.
11. G. E. Ham, J. Org. Chem., 1964, 29, 3052.
12. O. Mitsunobu, Synthesis, 1981, 1.