Asymmetric dihydroxylation with silica-anchored alkaloids

Abstract

Diols with excellent enantiomeric excesses are obtained from unfunctionalised alkenes in high yields by osmium-catalyseddihydroxylations using silica-bound pyrimidine and pyrazino-pyridazine ligands.

References

1. H. C. Kolb, S. VanNieuwenhze and K. B. Sharpless, Chem. Rev., 1994, 94, 2483.
2. E. N. Jacobsen, I. Markó, W. S. Mungall, G. Schroeder and K. B. Sharpless, J. Am. Chem. Soc., 1988, 110, 1968.
3. (a) H. Becker and K. B. Sharpless, Angew. Chem., 1996, 108, 447; Angew. Chem., Int. Ed. Engl., 1996, 35, 448; (b) H. Becker, S. B. King, M. Taniguchi, K. P. M. Vanhessche and K. B. Sharpless, J. Org. Chem., 1995, 60, 3940; (c) K. B. Sharpless, W. Amberg, Y. L. Bennani, G. A. Crispino, J. Hartung, K.-S. Jeong, H.-L. Kwong, K. Morikawa, Z.-M. Wang, D. Xu and X.-L. Zhang, J. Org. Chem., 1992, 57, 2768; (d) E. J. Corey, A. Guzman-Perez and M. C. Noe, J. Am. Chem. Soc., 1995, 117, 10805.
4. (a) B. M. Kim and K. B. Sharpless, Tetrahedron Lett., 1990, 31, 3003; (b) D. Pini, A. Petri, A. Nardi, C. Rosini and P. Salvadori, Tetrahedron Lett., 1991, 32, 5175; (c) B. B. Lohray, E. Nandanan and V. Bhushan, Tetrahedron Lett., 1994, 35, 6559; (d) C. E. Song, E. J. Roth, S.-y. Lee and I. O. Kim, Tetrahedron: Asymmetry, 1995, 6, 2687; (e) D. Pini, A. Petri and P. Salvadori, Tetrahedron, 1994, 50, 11 321; (f) A. Petri, D. Pini, S. Rapaccini and P. Salvadori, Chirality, 1995, 7, 580; (g) C. E. Song, J. W. Yang, H. J. Ha and S.-y. Lee, Tetrahedron: Asymmetry, 1996, 7, 645; (h) P. Salvadori, D. Pini and A. Petri, J. Am. Chem. Soc., 1997, 119, 6929 and references cited therein.
5. For examples of other silica-supported alkaloids see: B. B. Lohray, E. Nandanan and V. Bhushan, Tetrahedron: Asymmetry, 1996, 7, 2805; C. E. Song, J. W. Yang and H.-J. Ha, Tetrahedron: Asymmetry, 1997, 8, 841.
6. C. Bolm and A. Gerlach, Angew. Chem., 1997, 109, 773; Angew. Chem., Int. Ed. Engl., 1997, 36, 773.
7. H. Han and K. D. Janda, J. Am. Chem. Soc., 1996, 118, 7632; H. Han and K. D. Janda, Tetrahedron Lett., 1997, 38, 1527; H. Han and K. D. Janda, Angew. Chem., 1997, 109, 1835; Angew. Chem., Int. Ed. Engl., 1997, 36, 1731.
8. D. J. Berrisford, C. Bolm and K. B. Sharpless, Angew. Chem., 1995, 107, 1159; Angew. Chem., Int. Ed. Engl., 1995, 34, 1050.