Oxymercuration of 2-benzyl-2-azabicyclo[2.2.1]hept-5-en-3-one: explanation of stereoselectivity

Abstract

References

1. N. Katagiri, M. Muto and C. Kaneko, Tetrahedron Lett., 1989, 30, 1645; J. Chen, M. Grim, C. Rock and K. Chan, Tetrahedron Lett., 1989, 30, 5543; R. Vince and M. Hua, J. Med. Chem., 1990, 33, 17; M. E. Jung and H. Rhee, J. Org. Chem., 1994, 59, 4719; N. Katagiri, M. Takebayashi, H. Kokufuda, K. Kanehira and M. Torihara, J. Org. Chem., 1997, 62, 1580.
2. S. J. C. Taylor, A. G. Sutherland, C. Lee, R. Wisdom, S. Thomas, S. M. Roberts and C. Evans, J. Chem. Soc., Chem. Commun., 1990, 1120; S. J. C. Taylor, R. McCague, R. Wisdom, C. Lee, K. Dickson, G. Ruecroft, F. O'Brien, J. Littlechild, J. Bevan, S. M. Roberts and C. Evans, Tetrahedron: Asymmetry, 1993, 4, 1117; C. F. Palmer, R. McCague, G. Ruecroft, S. Savage, S. J. C. Taylor and C. Ries, Tetrahedron Lett., 1996, 37, 4601.
3. B. L. Bray, S. C. Dolan, B. Halter, W. Lackey, M. B. Schilling and D. J. Tapolczay, Tetrahedron Lett., 1995, 36, 4483; C. D. Maycock, M. T. Barros, A. G. Santos and L. S. Godinho, Tetrahedron Lett., 1993, 34, 7985; A. D. Borthwick, A. J. Crame, A. M. Exall and G. G. Weingarten, Tetrahedron Lett., 1994, 35, 7677.
4. C. F. Palmer, B. Webb, S. Broad, S. Casson, R. McCague, A. J. Willetts and S. M. Roberts, Bioord. Med. Chem. Lett., 1997, 7, 1299.
5. C. F. Palmer, K. P. Parry, S. M. Roberts and V. Sik, J. Chem. Soc., Perkin Trans. 1, 1992, 1021.
6. F. I. Carroll, P. Abraham, S. Chemburkar, X.-C. He, S. W. Mascarella, Y. W. Kwon and D. J. Triggle, J. Med. Chem., 1992, 35, 2184.
7. Y. F. Shealy and C. A. O'Dell, Tetrahedron Lett., 1969, 2231; C. F. Palmer, K. P. Parry and S. M. Roberts, J. Chem. Soc., Perkin Trans. 1, 1991, 484.
8. A similar rationale has been proposed previously to explain the products of phenylselenylation of the N-tosyl lactam 1(R = Ts)⁵ and more recently the iodination of some ring opened analogues: A. Toyota, Y. Ono and C. Kaneko, Tetrahedron Lett., 1995, 36, 6123.
9. W. C. Faith, C. A. Booth, B. M. Foxman and B. B. Snider, J. Org. Chem., 1985, 50, 1983.
10. M. B. Hursthouse, K. M. Abdul Malik, D. E. Hibbs, S. M. Roberts, A. J. H. Seago, V. Sik and R. Storer, J. Chem. Soc., Perkin Trans. 1, 1995, 2419.
11. R. C. Cermak and R. Vince, Tetrahedron Lett., 1981, 22, 2331.