The asymmetric Heck reaction: Recent developments and applications of new palladium diphenylphosphinopyrrolidine complexes

Topics in Catalysis

Volumn 4, Issue 3-4, 1997, Pages 311-326

  Guiry, Patrick J ^a   Hennessy, Alan J ^a   Cahill, John P ^a  

^a UNIVERSITY COLLEGE DUBLIN   (Ireland)

Author keywords

Asymmetric Heck; Chiral diphosphines; Chiral phosphinamines; Diphenylphosphinopyrrolidines; Intermolecular Heck; Intramolecular cyclisations; Palladium catalysis

Indexed keywords

EID: 0001423916     PISSN: 10225528     EISSN: None     Source Type: Journal    
DOI: 10.1023/a:1019121113063     Document Type: Article

References (34)

1. For an overview see R. Noyori, Asymmetric Catalysis in Organic Synthesis (Wiley, New York, 1994) ch. 2.
2. R.A. Johnson and K.B. Sharpless, in: Catalytic Asymmetric Synthesis, ed. I. Ojima (VCH, New York, 1993) ch. 4.
3. H.C. Kolb, M.S. Van Nieuwenhuize and K.B. Sharpless, Chem. Rev. 95 (1994) 2483.
4. (a) C.G. Frost. J. Howarth and J.M.J. Williams, Tetrahedron Asymmetry 3 (1992) 1089;
5. (b) For a general review of metal catalysed allylic substitutions see B.M. Trost and D.L. Van Dranken, Chem. Rev. 96 (1996) 395.
6. T. Hayashi, in: Catalytic Asymmetric Synthesis, ed. I. Ojima (VCH, New York, 1993) ch. 7.
7. For a mini-review of the asymmetric Heck reaction see K. Kondo, M. Sodeoka, M. Mori and M. Shibasaki, Synthesis (1993) 920.
8. (a) A. de Meijere and F.E. Meyer, Angew. Chem., Int. Ed. Engl. 28 (1994) 2379;
9. (b) W. Cabri and I. Candiani, Ace. Chem. Res. 28 (1995) 2;
10. (c) T. Jeffery, in: Advances in Metal-Organic Chemistry, Vol. 5 (JAI Press Inc., 1996) pp. 153-260.
11. R.F. Heck, J. Am. Chem. Soc. 90 (1968) 5518.
12. J.M. Brown, P.J. Guiry and A. Wienand, in: Principles of Molecular Recognition, eds. A.D. Buckingham, A.C. Legon and S.M. Roberts (Chapman and Hall, Glasgow, 1993) ch. 4.
13. L.S. Hegedus, in: Organometallics in Synthesis, ed. M. Schlosser (Wiley, Chichester, 1994) p. 383.
14. E.G. Samsel and J.R. Norton, J. Am. Chem. Soc. 106 (1984) 5505.
15. (a) R.C Larock, W.H. Gong and B.E. Baker, Tetrahedron Lett. 30 (1989) 2603;
16. (b) R.C Larock and W.H. Gong, J. Org. Chem. 54 (1989) 2047.
17. T. Jeffery, Tetrahedron Lett. 26 (1985) 2667.
18. F. Ozawa, A. Kubo and T. Hayashi, Tetrahedron Lett. 33 (1992) 1485.
19. F. Ozawa, A. Kubo, Y Matsumoto and T. Hayashi, Organometallics 12 (1993) 4188.
20. S. Hillers and O. Reiser, Tetrahedron Lett. 34 (1993) 2505.
21. (a) S. Hillers, A. Niklaus and O. Reiser, J. Org. Chem. 58 (1993) 3169;
22. (b) S. Hillers and O. Reiser, Synlett (1995) 153;
23. (c) S. Hillers, S. Sartori and O. Reiser, J. Am. Chem. Soc. 118 (1996) 2087.
24. F. Ozawa, Y Matsumoto and T. Hayashi, Tetrahedron Lett. 34 (1993) 2505.
25. T. Sakamoto, Y Kondo and H. Yamanaka, Tetrahedron Lett. 33 (1992) 6845.
26. C. Sonesson, M. Larhed, C. Nyqvist and A. Hallberg, J. Org. Chem. 61 (1996) 4763.
27. J.M. Brown, D.I. Hulmes and P.J. Guiry, Tetrahedron 50 (1994) 4493;
28. For a recent example see K.H. Ahn, C.-W. Cho, J. Park and S. Lee, Tetrahedron Asymmetry 8 (1997) 1179 and references therein.
29. (a) A. Pfaltz, Acta Chem. Scand. 50 (1996) 189 and references therein;
30. (b) J.M.J. Williams, Synlett (1996) 705;
31. (c) J. Sprinz, G. Knühl, P. Sennhenn, C. Lefeber, T. Feucht and G. Helmchen, Pure Appl. Chem. 69 (1997) 513.
32. O. Loiseleur, P. Meier and A. Pfaltz, Angew. Chem., Int. Ed. Engl. 35 (1996) 200.
33. H. Kubota, M. Nakijima and K. Koga, Tetrahedron Lett. 34 (1993) 8135.
34. H. Kubota and K. Koga, Tetrahedron Lett. 35 (1994) 6689.