Asymmetric catalytic intramolecular hydroacylation of 4-substituted pent-4-enals to β-substituted cyclopentanones

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

Richard W. Barnhart, David A. McMorran and B. Bosnich


Abstract

The catalyst, [Rh(S,S-Me-duphos)(acetone)2]+, rapidly and efficiently converts 4-substituted pent-4-enals bearing primary and secondary substituents to the corresponding cyclopentanones and for a variety of substituents the ee was found to range from 93 to 96% at 25 °C.


References

  1. D. P. Fairlie and B. Bosnich, Organometallics, 1988, 7, 936 CrossRef CAS .
  2. D. P. Fairlie and B. Bosnich, Organometallics, 1988, 7, 946 CrossRef CAS .
  3. K. Sakai, J. Ide, O. Oda and N. Nakamura, Tetrahedron Lett., 1972, 1287 CrossRef CAS ; C. F. Lochow and R. G. Miller, J. Am. Chem. Soc., 1976, 98, 1281 CrossRef CAS ; R. E. Campbell, C. F. Lochow, K. P. Vora and R. G. Miller, J. Am. Chem. Soc., 1980, 102, 5824 CrossRef ; J. W. Suggs, J. Am. Chem. Soc., 1978, 100, 640 CrossRef CAS ; R. C. Larock, K. Oertle and G. F. Potter, J. Am. Chem. Soc., 1980, 102, 190 CrossRef CAS ; K. P. Vora, C. F. Lachow and R. G. Miller, J. Org. Chem., 1980, 192, 257 CrossRef CAS ; R. E. Campbell and R. G. Miller, J. Org. Chem., 1980, 186, C27 CAS ; D. Milstein, J. Chem. Soc., Chem. Commun., 1982, 1357 RSC ; B. R. James and C. G. Young, J. Chem. Soc., Chem. Commun., 1983, 1215 RSC ; K. Sakai, Y. Ishiguor, K. Funakoshi, K. Ueno and H. Suemune, Tetrahedron Lett., 1984, 40, 961 CrossRef CAS ; B. R. James and C. G. Young, J. Org. Chem., 1985, 285, 321 CrossRef CAS ; J. W. Suggs and M. J. Wovkulich, Organometallics, 1985, 4, 1101 CrossRef CAS ; Y. Taura, M. Tanaka, K. Funakoshi and K. Sakai, Tetrahedron Lett., 1989, 30, 6349 CrossRef CAS ; K. P. Gable and G. A. Benz, Tetrahedron Lett., 1991, 32, 3473 CrossRef CAS ; Y. Taura, M. Tanaka, X. Wu, K. Funakoshi and K. Sakai, Tetrahedron, 1991, 47, 4879 CrossRef CAS ; X. Wu, K. Funakoshi and K. Sakai, Tetrahedron Lett., 1992, 33, 6331 CrossRef CAS ; X. Wu, K. Funakoshi and K. Sakai, Tetrahedron Lett., 1993, 34, 5927 CrossRef CAS ; P. Eilbrach, A. Gersmeier, D. Lennartz and T. Huber, Synthesis, 1994, 330 .
  4. R. W. Barnhart, X. Wang, P. Noheda, S. H. Bergens, J. Whelan and B. Bosnich, J. Am. Chem. Soc., 1994, 116, 1821 CrossRef CAS .
  5. D. Enders and H. Eichenauer, Tetrahedron Lett., 1977, 191 CrossRef CAS .
  6. For R = Me and Pri, see: G. H. Posner, L. L. Frye and M. Hulce, Tetrahedron, 1984, 40, 1401 Search PubMed ; D. F. Taber and K. Raman, J. Am. Chem. Soc., 1983, 105, 5935 CrossRef CAS ; G. H. Posner and M. Hulce, Tetrahedron Lett., 1994, 25, 379 CrossRef CAS .
  7. P. Albano, M. Aresta and M. Manassero, Inorg. Chem., 1980, 19, 1069 CrossRef CAS .
  8. R. W. Barnhart and B. Bosnich, Organometallics, 1995, 14, 4343 CrossRef CAS .