Platinum catalysed 1,4-diboration of α,β-unsaturated ketones

Abstract

Diborane(4) compounds react with α,β-unsaturated ketones to give the 1,4-addition product in the presence of a platinum catalyst at 80 °C.

References

1. K. Burgess and M. J. Ohlmeyer, Chem. Rev., 1991, 91, 1179; I. Beletskaya and A. Pelter, Tetrahedron, 1997, 53, 4957.
2. R. T. Baker, P. Nguyen, T. B. Marder and S. A. Westcott, Angew. Chem., Int. Ed. Engl., 1995, 34, 1336.
3. T. Ishiyama, M. Yamamoto and N. Miyaura, Chem. Commun., 1997, 689.
4. C. N. Iverson and M. R. Smith, Organometallics, 1997, 16, 2757.
5. (a) T. Ishiyama, N. Matsuda, N. Miyaura and A. Suzuki, J. Am. Chem. Soc., 1993, 115, 11 018; (b) F. Ozaura, A. Suzuki and N. Miyaura, Organometallics, 1996, 15, 713; (c) C. N. Iverson and M. R. Smith, J. Am. Chem. Soc., 1995, 117, 4403; (d) C. N. Iverson and M. R. Smith, Organometallics, 1996, 15, 5155; (e) M. J. G. Lesley, P. Nguyen, N. J. Taylor, T. B. Marder, A. J. Scott, W. Clegg and N. C. Norman, Organometallics, 1996, 15, 5137.
6. T. Ishiyama, M. Yamamoto and N. Miyaura, Chem. Commun., 1996, 2073.
7. C. Dai, M. J. G. Lesley, T. B. Marder, N. C. Norman and C. R. Rice, Main Group Chem. News, 1997, in the press.
8. D. A. Evans and G. C. Fu, J. Org. Chem., 1990, 55, 5678.
9. Y. Matsumoto and T. Hayashi, Synlett, 1991, 349.
10. H. Nöth, Z. Naturforsch., Teil B, 1984, 39, 1463.
11. F. J. Lawlor, N. C. Norman, N. L. Pickett, E. G. Robins, P. Nguyen, M. J. G. Lesley, T. B. Marder, J. A. Ashmore and J. C. Green, Inorg. Chem., in the press.
12. A. Fauve and H. Veschambre, J. Org. Chem., 1988, 53, 5215.