Catalytic asymmetric cyclopropanation of electron deficient alkenes mediated by chiral sulfides

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Varinder K. Aggarwal, Helen W. Smith, Ray V. H. Jones and Robin Fieldhouse


Abstract

Catalytic asymmetric cylopropanation of enones has been achieved using diazo compounds, catalytic quantities of a metal catalyst and a camphor-derived thioacetal; this sulfide shows exceptionally high levels of enantioselectivity.


References

  1. H. N. C. Wong, M. Y. Hon, C. W. Tse, Y. C. Yip, J. Tanko and T. Hudlicky, Chem. Rev., 1989, 89, 165 CrossRef CAS; T. Hudlicky and J. W. Reed, Comprehensive Organic Synthesis, ed. B. M. Trost and I. Fleming, Pergamon, Oxford, 1991, vol. 5, p. 899 Search PubMed.
  2. J. Salaun, Chem. Rev., 1989, 89, 1247 CrossRef CAS.
  3. V. K. Singh, A. DattaGupta and G. Sekar, Synthesis, 1997, 137 CrossRef CAS.
  4. H. E. Simmons and R. D. Smith, J. Am. Chem. Soc., 1958, 80, 5323 CrossRef CAS.
  5. H. E. Simmons, T. L. Cairns, S. A. Vladuchick and C. M. Hoiness, Org. React., 1973, 20, 1 CAS.
  6. A. B. Charette and H. Juteau, J. Am. Chem. Soc., 1994, 116, 2651 CrossRef CAS.
  7. A. B. Charette, S. Prescott and C. Brochu, J. Org. Chem., 1995, 60, 1081 CrossRef CAS.
  8. D. A. Evans, K. A. Woerpel, M. M. Hinman and M. M. Faul, J. Am. Chem. Soc., 1991, 113, 726 CrossRef CAS.
  9. H. M. L. Davies, N. J. S. Huby, W. R. Cantrell, Jr. and J. L. Olive, J. Am. Chem. Soc., 1993, 115, 9468 CrossRef CAS.
  10. R. E. Lowenthal and S. Masumune, Tetrahedron Lett., 1991, 32, 7373 CrossRef CAS.
  11. For an example of metal carbenoid addition to an electron deficient alkene, see T. Hudlicky and R. P. Short, J. Org. Chem., 1982, 47, 1522 Search PubMed However, in this example the reaction is intramolecular, which no doubt facilitates the process. It was also noted in this example that marginally higher yields were obtained in the presence of sulfides, suggesting the intermediacy of a sulfur ylide. We thank one of the referees for bringing this paper to our attention.
  12. C. R. Johnson and C. W. Schroek, J. Am. Chem. Soc., 1973, 95, 7418 CrossRef CAS.
  13. S. G. Pyne, Z. Dong, B. W. Skelton and A. H. White, J. Org. Chem., 1997, 62, 2337 CrossRef CAS.
  14. V. K. Aggarwal, J. G. Ford, A. Thompson, R. V. H. Jones and M. Standen, J. Am. Chem. Soc., 1996, 118, 7004 CrossRef CAS.
  15. V. K. Aggarwal, H. Abdel-Rahman, F. Li, R. V. H. Jones and M. C. H. Standen, Chem. Eur. J., 1996, 2, 1024 CrossRef CAS.
  16. V. K. Aggarwal, A. Thompson, R. V. H. Jones and M. C. H. Standen, J. Org. Chem., 1996, 61, 8368 CrossRef CAS.
  17. E. Block, The Chemistry of the Sulphonium Group, ed. C. J. M. Stirling and S. Patai, Wiley, New York, 1981, p. 673 Search PubMed.
  18. I. E. Markó, Comprehensive Organic Synthesis, ed. B. M. Trost and I. Fleming, Pergamon, Oxford, 1991, vol. 3, p. 913 Search PubMed.
  19. W. Ando, M. Yamada, E. Matsuzaki and T. Migita, J. Org. Chem., 1972, 37, 3791 CrossRef CAS.
  20. N. A. Nesmayanov and V. A. Kalyavin, Org. Soedin. Sery, 1980, 2, 330 Search PubMed; Chem. Abstr., 1981, 94, 192 063 Search PubMed.
  21. M. Yoshimine and M. J. Hatch, J. Am. Chem. Soc., 1967, 89, 5831 CrossRef CAS.
  22. M. Hetschko and J. Gossleck, Chem. Ber., 1973, 106, 996 CAS.
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