Palladium catalysed heck and enantioselective allylic substitution reactions using reverse phase silica supports

Tetrahedron Letters

Volumn 40, Issue 39, 1999, Pages 7147-7150

  Anson, Michael S ^a   Mirza, Amin R ^b   Tonks, Louise ^b   Williams, Jonathan M J ^b  

^a GLAXOSMITHKLINE   (United Kingdom)

^b University of Bath   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL COMPOUND; PALLADIUM; SILICON DIOXIDE;

ARTICLE; CATALYSIS; LEACHING; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0033600767     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01485-9     Document Type: Article

References (15)

1. 1. For reviews on supported polar liquid phase catalysis, see; (a) M. E. Davis, Chemtech, 1992, 498 and
2. (b) M. S. Anson, M. P. Leese, L. Tonks and J. M. J. Williams, J. Chem. Soc.. Dalton Trans, 1998, 3529.
3. 2. L. Tonks, M. S. Anson, K. Hellgardt, A. R. Mirza, D. F. Thompson and J. M. J. Williams Tetrahedron Lett., 1997, 38, 4319. A. R. Mirza, M. S. Anson, K. Hellgardt, M. P. Leese, D. F. Thompson, L. Tonks and J. M. J. Williams, Org. Proc. Res and Dev., 1998, 2, 325. For examples of Heck reactions using water-soluble ligands, see, J. Kiji, T. Okano and T. Hasegawa, J. Mol. Cat. A, 1995, 97, 73. H. Dibowski and F. P. Schmidtchen, Tetrahedron, 1995, 51, 2325.
4. 2. L. Tonks, M. S. Anson, K. Hellgardt, A. R. Mirza, D. F. Thompson and J. M. J. Williams Tetrahedron Lett., 1997, 38, 4319. A. R. Mirza, M. S. Anson, K. Hellgardt, M. P. Leese, D. F. Thompson, L. Tonks and J. M. J. Williams, Org. Proc. Res and Dev., 1998, 2, 325. For examples of Heck reactions using water-soluble ligands, see, J. Kiji, T. Okano and T. Hasegawa, J. Mol. Cat. A, 1995, 97, 73. H. Dibowski and F. P. Schmidtchen, Tetrahedron, 1995, 51, 2325.
5. 2. L. Tonks, M. S. Anson, K. Hellgardt, A. R. Mirza, D. F. Thompson and J. M. J. Williams Tetrahedron Lett., 1997, 38, 4319. A. R. Mirza, M. S. Anson, K. Hellgardt, M. P. Leese, D. F. Thompson, L. Tonks and J. M. J. Williams, Org. Proc. Res and Dev., 1998, 2, 325. For examples of Heck reactions using water-soluble ligands, see, J. Kiji, T. Okano and T. Hasegawa, J. Mol. Cat. A, 1995, 97, 73. H. Dibowski and F. P. Schmidtchen, Tetrahedron, 1995, 51, 2325.
6. 2. L. Tonks, M. S. Anson, K. Hellgardt, A. R. Mirza, D. F. Thompson and J. M. J. Williams Tetrahedron Lett., 1997, 38, 4319. A. R. Mirza, M. S. Anson, K. Hellgardt, M. P. Leese, D. F. Thompson, L. Tonks and J. M. J. Williams, Org. Proc. Res and Dev., 1998, 2, 325. For examples of Heck reactions using water-soluble ligands, see, J. Kiji, T. Okano and T. Hasegawa, J. Mol. Cat. A, 1995, 97, 73. H. Dibowski and F. P. Schmidtchen, Tetrahedron, 1995, 51, 2325.
7. 3. The derivatisation method is based on the a literature example: P.D.G. Dean, W.S. Johnson and F. Middle Affinity Chromatography: A Practical Approach, Oxford University Press, 1985, p25-28.
8. 4. Davisil can be purchased from Supelco UK (a division of the Sigma-Aldrich Company Ltd), Fancy Road. Poole, Dorset, BH12 4QH, UK.
9. 5. Palladium catalysts based on the tri-o-tolylphosphine ligand are known to provide enhanced reactivity in Heck reactions C.B. Ziegler Jr. and R.F. Heck, J. Org. Chem., 1978, 43, 2949.
10. 6. C. G. Frost, J. Howarth and J.M.J. Williams, Tetrahedron: Asymmetry, 1992, 3, 1089. B.M. Trost and D.L. VanVranken, Chem. Rev., 1996, 96, 395.
11. 6. C. G. Frost, J. Howarth and J.M.J. Williams, Tetrahedron: Asymmetry, 1992, 3, 1089. B.M. Trost and D.L. VanVranken, Chem. Rev., 1996, 96, 395.
12. 7. see reference 2 and also P. Schneider, F. Quignard and A. Choplin, New J. Chem., 1996, 20, 545.
13. 8. This ligand was independently reported by three groups in J. Sprinz, and G. Helmchen, Tetrahedron Lett. 1993, 34, 1769. P. von Matt and A. Pfaltz, Angew. Chem., Int. Ed. Engl., 1993, 32, 566. G. J. Dawson, C. G. Frost, J. M. J. Williams and S. J. Coote, Tetrahedron Lett., 1993, 34, 3149.
14. 8. This ligand was independently reported by three groups in J. Sprinz, and G. Helmchen, Tetrahedron Lett. 1993, 34, 1769. P. von Matt and A. Pfaltz, Angew. Chem., Int. Ed. Engl., 1993, 32, 566. G. J. Dawson, C. G. Frost, J. M. J. Williams and S. J. Coote, Tetrahedron Lett., 1993, 34, 3149.
15. 8. This ligand was independently reported by three groups in J. Sprinz, and G. Helmchen, Tetrahedron Lett. 1993, 34, 1769. P. von Matt and A. Pfaltz, Angew. Chem., Int. Ed. Engl., 1993, 32, 566. G. J. Dawson, C. G. Frost, J. M. J. Williams and S. J. Coote, Tetrahedron Lett., 1993, 34, 3149.