Efficient RhII binaphthol phosphate catalysts for enantioselective intramolecular tandem carbonyl ylide formation–cycloaddition of α-diazo-β-keto esters

(Note: The full text of this document is currently only available in the PDF Version )

David M. Hodgson, Paul A. Stupple and Craig Johnstone


Abstract

Catalytic enantioselective tandem carbonyl ylide formation–cycloadditions of α-diazo-β-keto ester 1 using 0.5 mol% dirhodium tetrakis(1,1′-binaphthyl-2,2′-diyl phosphate) catalysts 7–9 and 14 to give the cycloadduct 3 in good yields and up to 90% ee are described.


References

  1. K. V. Gothelf and K. A. Jørgensen, Chem. Rev., 1998, 98, 863 CrossRef CAS; A. Padwa and M. D. Weingarten, Chem. Rev., 1996, 96, 223 CrossRef CAS.
  2. D. M. Hodgson, P. A. Stupple and C. Johnstone, Tetrahedron Lett., 1997, 38, 6471 CrossRef CAS.
  3. A carboxamidate catalyst gave racemic cycloadduct, see ref. 2.
  4. M. P. Doyle and D. C. Forbes, Chem. Rev., 1998, 98, 911 CrossRef CAS.
  5. H. Suga, H. Ishida and T. Ibata, Tetrahedron Lett., 1998, 39, 3165 CrossRef CAS.
  6. S. Kitagaki, M. Anada, O. Kataoka, K. Matsuno, C. Umeda, N. Watanabe and S. Hashimoto, J. Am. Chem. Soc., 1999, 121, 1417 CrossRef CAS.
  7. P. A. Stupple, unpublished results.
  8. M. C. Pirrung and J. Zhang, Tetrahedron Lett., 1992, 33, 5987 CrossRef CAS.
  9. N. McCarthy, M. A. McKervey, T. Ye, M. McCann, E. Murphy and M. P. Doyle, Tetrahedron Lett., 1992, 33, 5983 CrossRef CAS.
  10. D. J. Cram, R. C. Helgeson, S. C. Peacock, L. J. Kaplan, L. A. Domeier, P. Moreau, K. Koga, J. M. Mayer, Y. Chao, M. G. Siegel, D. H. Hoffman and G. D. Y. Sogah, J. Org. Chem., 1978, 43, 1930 CrossRef CAS.
  11. H. Sasai, T. Tokunaga, S. Watanabe, T. Suzuki, N. Itoh and M. Shibasaki, J. Org. Chem., 1995, 60, 7388 CrossRef CAS; M. Terada, Y. Motoyama and K. Mikami, Tetrahedron Lett., 1994, 35, 6693 CrossRef CAS.
  12. U.S. Pat., 3 848 030, 1974 Search PubMed; Chem. Abstr., 1973, 78, 43129b Search PubMed.
  13. T. Hamada, T. Fukuda, H. Imanishi and T. Katsuki, Tetrahedron, 1996, 52, 515 CrossRef CAS.
  14. B. J. Brisdon, R. England, K. Reza and M. Sainsbury, Tetrahedron, 1993, 49, 1103 CrossRef CAS.
  15. G. A. Olah, S. Narang, B. G. B. Gupta and R. Malhotra, J. Org. Chem., 1979, 44, 1247 CrossRef CAS.
  16. H. J. Callot and F. Metz, Tetrahedron, 1985, 41, 4495 CrossRef CAS.
Click here to see how this site uses Cookies. View our privacy policy here.