Determination of absolute configuration of (π-Allyl)palladium complexes by NMR spectroscopy and stereoselective complexation

Chemistry - A European Journal

Volumn 7, Issue 2, 2001, Pages 396-403

  Gogoll, Adolf ^a   Johansson, Charlotte ^a   Axén, Andreas ^a   Grennberg, Helena ^a  

^a UPPSALA UNIVERSITY   (Sweden)

Author keywords

Absolute configuration; Allyl ligands; Chelates; Chiral resolution; NMR spectroscopy; Palladium

Indexed keywords

CHELATING AGENT; LIGAND; N,N' BIS(PHENYLETHYL)BISPIDINE; PALLADIUM COMPLEX; PHENYL GROUP; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CHIRALITY; COMPLEX FORMATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOCHEMISTRY;

EID: 0035910437     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (59)

1. a) B. M. Trost, D. L. Van Vranken, Chem. Rev. 1996, 96, 395;
2. b) B. M. Trost, Acc. Chem. Res. 1996, 29, 355;
3. c) P. S. Pregosin, G. Trabesinger, J. Chem. Soc. Dalton Trans. 1998, 727;
4. d) A. Albinati, P. S. Pregosin, K. Wick, Organometallics 1996, 15, 2419;
5. e) A. Togni, U. Burckhardt, V. Gramlich, P. S. Pregosin, R. Salzmann, J. Am. Chem. Soc. 1996, 118, 1031;
6. f) P. Barbaro, P. S. Pregosin, R. Salzmann, A. Albinati, Kunz, R. W. Organometallics 1995, 14, 5160;
7. g) E. Peña-Cabrera, P.-O. Norrby, M. Sjögren, A. Vitagliano, V. De Felice, J. Oslob, S. Ishii, D. O'Neill, B. Åkermark, P. Helquist, J. Am. Chem. Soc. 1996, 118, 4299;
8. h) A. Togni, Tetrahedron: Asymmetry 1991, 2, 683.
9. a) J. W. Faller, M. J. Incovino, M. E. Thomsen, J. Am. Chem. Soc. 1969, 97, 518;
10. b) J. W. Faller, M. E. Thomsen, J. Am. Chem. Soc. 1969, 91, 6871;
11. c) J. W. Faller, M. E. Thomsen, M. J. Mattina, J. Am. Chem. Soc. 1971, 93, 2642;
12. d) P. Corradini, G. Maglio, A. Musco, G. Paiaro, Chem. Commun. 1966, 618;
13. e) J. Lukas, P. W. N. M. van Leeuwen, H. C. Volger, A. P. Kouwenhoven, J. Organomet. Chem. 1973, 47, 153.
14. a) J. L. Bookham, W. McFarlane, J. Chem. Soc. Chem. Commun. 1993, 1352;
15. b) W. McFarlane, J. D. Swarbrick, J. L. Bookham, J. Chem. Soc. Dalton Trans. 1998, 3233.
16. Further signals may be observed if the relative orientation of the two π-allyl groups can change, irrespective of their chirality: a) A. C. Albéniz, P. Espinet, C. Foces-Foces, F. H. Cano, Organometallics 1990, 9, 1079;
17. b) J. T. Martin, J. D. Oslob, B. Åkermark, P.-O. Norrby, Acta Chem. Scand. 1995, 49, 888.
18. a) A. Gogoll, H. Grennberg, A. Axén, Organometallics 1997, 16, 1167;
19. b) A. Gogoll, H. Grennberg, A. Axén, Organometallics 1998, 17, 5248.
20. a) D. J. Gallagher, S. Wu, N. A. Nicolic, P. Beak, J. Org. Chem. 1995, 60, 8184.;
21. b) N. S. Zefirov, S. V. Rogozina, Tetrahedron 1974, 30, 2345.
22. a) A. Gogoll, H. Grennberg, A. Axén, Magn. Reson. Chem. 1997, 35, 13;
23. eq. The methine proton only has an NOE with the axial protons and the ortho-phenyl protons only with the equatorial protons.
24. D. St. C. Black, M. A. Horsham, M. Rose, Tetrahedron 1995, 51, 4819;
25. b) N. S. Zefirov, V. A. Palyulin in Topics in Stereochemistry, Vol. 20, (Eds.: E. L. Eliel, S. H. Wilen), Wiley, Chichester, 1991, p. 171.
26. A. Gogoll, H. Grennberg, A. Axén, Magn. Reson. Chem. 1997, 35, 13.
27. M. Sjögren, S. Hansson, P.-O. Norrby, B. Åkermark, Organometallics 1992, 11, 3954.
28. a) D. H. Farrar, N. C. Payne, J. Am. Chem. Soc. 1985, 107, 2054;
29. b) A. Togni, U. Burckhardt, V. Gramlich, P. S. Pregosin, R. Salzmann, J. Am. Chem. Soc. 1996, 118, 1031;
30. c) A. Togni, G. Rihs, P. S. Pregosin, C. Ammann, Helv. Chim. Acta 1990, 73, 723;
31. d) A. Pfaltz, Acta Chem. Scand. 1996, 50, 189.
32. P. Dierks, S. Ramdeehul, L. Barloy, A. De Cian, J. Fischer, P. C. J. Kamer, P. W. N. M. van Leeuwen, J. A. Osborn, Angew. Chem. 1998, 110, 3299; Angew. Chem. Int. Ed. 1998, 37, 3116.
33. P. Dierks, S. Ramdeehul, L. Barloy, A. De Cian, J. Fischer, P. C. J. Kamer, P. W. N. M. van Leeuwen, J. A. Osborn, Angew. Chem. 1998, 110, 3299; Angew. Chem. Int. Ed. 1998, 37, 3116.
34. a) K. Vrieze, H. C. Volger, P. W. N. M. van Leeuwen, Inorg. Chim. Acta Rev. 1969, 109;
35. b) A. Albinati, C. J. Ammann, P. S. Pregosin, H. Rüegger, Organometallics 1990, 9, 1826;
36. c) A. Gogoll, J. Örnebro, H. Grennberg, J.-E. Bäckvall, J. Am. Chem. Soc. 1994, 116, 3631.
37. F. Bökman, A. Gogoll, O. Bohman, L. G. M. Pettersson, H. O. G. Siegbahn, Organometallics 1992, 11, 1784.
38. a) H. Grennberg, V. Langer, J.-E. Bäckvall, J. Chem. Soc. Chem. Commun. 1991, 1190;
39. b) C. Jonasson, M. Kritikos, J.-E. Bäckvall, K. J. Szabó, Chem. Eur. J. 2000, 6, 432.
40. B. M. Trost, P. E. Strege, Tetrahedron 1974, 30, 2603.
41. Computations with semiempirical methods by using Spartan 5.1.1. with PM3-TM have been performed.
42. 1 symmetry, additional diastereomeric complexes are possible, see for example, ref. [1g].
43. a) G. R. Sullivan, J. A. Dale, H. S. Mosher, J. Org. Chem. 1973, 38, 2143;
44. b) B. M. Trost, R. C. Bunt, Sh. R. Pulley, J. Org. Chem. 1994, 59, 4202;
45. c) B. M. Trost, J. L. Belletire, S. Godleski, P. G. McDougal, J. M. Balkovec, J. Org. Chem. 1986, 51, 2370
46. d) Sh. K. Latypov, J. M. Seco, E. Quiñoá, R. Riguera, J. Org. Chem. 1996, 61, 8569.
47. L. Mueller, J. Magn. Reson. 1987, 72, 191.
48. a) G. Bodenhausen, D. J. Ruben, Chem. Phys. Lett. 1980, 69, 185;
49. b) A. M. Torres, T. T. Nakashima, R. E. D. McClung, J. Magn. Reson. A 1993, 102, 219.
50. K. E. Kövér, O. Prakash, V. J. Hruby, Magn. Reson. Chem. 1993, 31, 231.
51. a) D. J. States, R. A. Haberkorn, D. J. Ruben, J. Magn. Reson. 1982, 48, 286;
52. b) G. Wider, S. Macura, A. Kumar, R. R. Ernst, K. Wüthrich, J. Magn. Reson. 1984, 56, 207.
53. A. A. Bothner-By, R. L. Stephens, J. M. Lee, C. D. Warren, R. W. Jeanloz, J. Am. Chem. Soc. 1984, 106, 811.
54. J. K. M. Sanders, J. D. Mersh in Progress in Nuclear Magnetic Resonance Spectroscopy, Vol. 15, (Eds.: J. W. Emsley, J. Feeney, L. H. Sutcliffe), Pergamon, Oxford, 1982, p. 353.
55. K. N. Welch, J. Chem. Soc. 1931, 673.
56. E. Buchta, S. Billenstein, Justus Liebigs Ann. Chem. 1966, 962, 42.
57. R. Hüttel, J. Kratzer, M. Bechter, Chem. Ber. 1961, 94, 766.
58. a) T. G. Appleton, J. D. Cotton, J. Chem. Educ. 1978, 55, 131;
59. b) B. Åkermark, B. Krakenberger, S. Hansson, A. Vitagliano, Organometallics 1987, 6, 620.