Substituent effects of ligands on asymmetric induction in a prototypical palladium-catalyzed allylation reaction: Making both enantiomers of a product in high optical purity using the same source of chirality

Journal of Organic Chemistry

Volumn 64, Issue 20, 1999, Pages 7601-7611

  Clyne, Dean S ^a   Mermet Bouvier, Yvan C ^a   Nomura, Nobuyoshi ^a   RajanBabu, T V ^a  

^a OHIO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PALLADIUM;

ARTICLE; CATALYSIS; CHIRALITY; COMPLEX FORMATION; LIGAND BINDING; SYNTHESIS;

EID: 0033214803     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9911387     Document Type: Article

References (73)

1. (a) Ojima, I. Catalytic Asymmetric Synthesis; VCH: Weinheim, 1993.
2. (b) Noyori, R. Asymmetric Catalysis in Organic Synthesis; John Wiley: New York, 1994.
3. (c) Brunner, H.; Zettlmeier, W. Handbook of Enantioselective Catalysis; VCH: Weinheim, 1993.
4. (a) Inoguchi, K.; Sakuraba, S.; Achiwa, K. Synlett 1992, 169 and references therein.
5. (b) Jacobsen, E. N.; Zhang, W.; Güler, M. L. J. Am. Chem. Soc. 1991, 113, 6703.
6. (c) Nishiyama, H.; Yamaguchi, S.; Kondo, M.; Itoh, K. J. Org. Chem. 1992, 57, 4306.
7. (d) RajanBabu, T. V.; Casalnuovo, A. L. J. Am. Chem. Soc. 1992, 114, 6265.
8. (e) RajanBabu, T. V.; Casalnuovo, A. L.; Ayers, T. A. In Advances in Catalytic Processes; Doyle, M., Ed.; JAI Press: Greenwich, CT, 1998; Vol. 2, p 1.
9. (f) Williams, J. M. J. Synlett 1996, 705.
10. (g) Schnyder, A.; Hintermann, L.; Togni, A. Angew. Chem., Int. Ed. Engl. 1995, 34, 931 and references therein.
11. (a) Casalnuovo, A. L.; RajanBabu, T. V.; Ayers, T. A.; Warren, T. H. J. Am. Chem. Soc. 1994, 116, 9869.
12. (b) RajanBabu, T. V.; Casalnuovo, A. L. J. Am. Chem. Soc. 1994, 118, 6325.
13. (c) Casalnuovo, A. L.; RajanBabu, T. V. In Chirality in Industry II; Collins, A. N., Sheldrake, G. N., Crosby, J., Eds.; John Wiley: Chichester, 1996; p 309.
14. (a) RajanBabu, T. V.; Ayers, T. A.; Casalnuovo, A. L. J. Am. Chem. Soc. 1994, 116, 4101.
15. (b) RajanBabu, T. V.; Ayers, T. A.; Halliday, G. A.; You, K. K.; Calabrese, J. C. J. Org. Chem. 1997, 62, 6012.
16. (c) RajanBabu, T. V.; Radetich, B.; You, K. K.; Ayers, T. A.; Casalnuovo, A. L.; Calabrese, J. C. J. Org. Chem. 1999, 64, 3429.
17. RajanBabu, T. V.; Ayers, T. A. Tetrahedron Lett. 1994, 35, 4295.
18. (a) Landis, C. R.; Halpern, J. J. Am. Chem. Soc. 1987, 109, 1746.
19. (b) Brown, J. M. Chem. Soc. Rev. 1993, 25.
20. (c) Bircher, H.; Bender, B. R.; von Philipsborn, W. Magn. Reson. Chem. 1993, 31, 293.
21. (d) Giovannetti, J. S.; Kelly, C. M.; Landis, C. R. J. Am. Chem. Soc. 1993, 115, 4040.
22. (a) Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395.
23. (b) Mackenzie, P. B.; Whelan, J.; Bosnich, B. J. Am. Chem. Soc. 1985, 107, 2046.
24. (c) von Matt, P.; Lloyd-Jones, G. C.; Minidis, A. B. E.; Pfaltz, A.; Macko, L.; Neuberger, M.; Zehnder, M.; Rüegger, H.; Pregosin, P. S. Helv. Chim. Acta 1995, 78, 265.
25. (d) Steinhagen, H.; Reggelin, M.; Helmchen, G. Angew. Chem., Int. Ed. Engl. 1997, 36, 2108.
26. (e) Evans, D. A.; Campos, K. R.; Tedrow, J. S.; Michael, F. E.; Gagné, M. R. J. Org. Chem. 1999, 64, 2994.
27. Hayashi, T. In ref 1a, p 325.
28. (a) Yamaguchi, M.; Shima, T.; Yamagishi, T.; Hida, M. Tetrahedron: Asymmetry 1991, 2, 663.
29. (b) Yamaguchi, M.; Yabuki, M.; Yamagishi, T.; Sakai, K.; Tsubomura, T. Chem. Lett. 1996, 241.
30. (a) Frost, C. G.; Howarth, J.; Williams, J. M. J. Tetrahedron: Asymmetry 1992, 3, 1089.
31. (b) Allen, J. V.; Coote, S. J.; Dawson, G. J.; Frost, C. G.; Martin, C. J.; Williams, J. M. J. J. Chem. Soc., Perkin Trans. 1 1994, 2065.
32. Sprinz, J.; Kiefer, M.; Helmchen, G.; Reggelin, M.; Huttner, G.; Walter, O.; Zsolnai, L. Tetrahedron Lett. 1994, 35, 1523.
33. Togni, A.; Breutel, C.; Schnyder, A.; Spindler, F.; Landert, H.; Tijani, A. J. Am. Chem. Soc. 1994, 116, 4062.
34. Brown, J. M.; Hulmes, D. I.; Guiry, P. J. Tetrahedron 1994, 50, 4493.
35. Andersson, P. G.; Harden, A.; Tanner, D.; Norrby, P.-O. Chem. Eur. J. 1995, 1, 12.
36. Seebach, D.; Devaquet, E.; Ernst, A.; Hayakawa, M.; Kühnle, F. N. M.; Schweizer, W. B.; Weber, B. Helv. Chim. Acta 1995, 78, 1636.
37. Pen̈a-Cabrera, E.; Norrby, P.-O.; Sjöegren, M.; Vitagliano, A.; De Felice, V.; Oslob, J.; Ishii, S.; O'Neill, D.; Akermark, B.; Helquist, P. J. Am. Chem. Soc. 1996, 118, 4299.
38. For a preliminary account, see: Nomura, N.; Mermet-Bouvier, Y. C.; RajanBabu, T. V. Synlett 1996, 745. While this manuscript was being reviewed another report dealing with electronic effects in Pd-catalyzed allylation appeared. Saitoh, A.; Misawa, M.; Morimoto, T. Synlett 1999, 483.
39. For a preliminary account, see: Nomura, N.; Mermet-Bouvier, Y. C.; RajanBabu, T. V. Synlett 1996, 745. While this manuscript was being reviewed another report dealing with electronic effects in Pd- catalyzed allylation appeared. Saitoh, A.; Misawa, M.; Morimoto, T. Synlett 1999, 483.
40. Trabesinger, G.; Albinati, A.; Feiken, N.; Kunz, R. W.; Pregosin, P. S.; Tschoerner, M. J. Am. Chem. Soc. 1997, 119, 6315.
41. (a) Dutta, D.; Majumdar, D. J. Phys. Org. Chem. 1991, 4, 611.
42. (b) White, D.; Coville, N. J. Adv. Organomet. Chem. 1994, 36, 95.
43. We have previously seen that in Rh-catalyzed asymmetric hydrogenation of dehydroamino acids, conformationally flexible ligands show more pronounced, and often predictable, electronic effects. See refs 4b and 4c.
44. Indeed diphenylphosphinite from binaphthol was one of the first chiral ligands used for enantioselective allylation of malonates. Trost, B. M.; Murphy, D. J. Organometallics 1986, 4, 1143. These workers were also among the first to prepare the 3,5-bis-TMS-aryl derivative. It is not apparent whether the switching of the enantioselection occurred with the allylation of the cyclic substrate that was studied, the increase in selectivity notwithstanding.
45. Pfaltz, A. Acc. Chem. Res. 1993, 26, 341.
46. (a) Åkermark, B.; Hansson, S.; Krakenberger, B.; Vitagliano, A.; Zetterberg, K. Organometallics 1984, 3, 679.
47. (b) Akermark, B.; Krakenberger, B.; Hansson, S.; Vitagliano, A. Organometallics 1987, 6, 620.
48. Barbaro, P.; Pregosin, P. S.; Salzmann, R.; Albinati, A.; Kunz, R. W. Organometallics 1905, 14, 5160.
49. Togni, A.; Burckhurdt, U.; Gramlich, V.; Pregosin, P. S.; Salzmann, R. J. Am. Chem. Soc. 1996, 118, 1031.
50. For definitions of λ and δ-conformations, see: (a) Kagan, H. B. Asymmetric Synthesis Using Organometallic Catalysts. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: Oxford, 1982; Vol. 8, p 463.
51. (b) Pavlov, V. A.; Klaunovskii, E. I.; Struchkov, Y. T.; Voloboev, A. A.; Yanovsky, A. I. J Mol. Catal. 1988, 44, 217.
52. Herrmann, J.; Pregosin, P. S.; Salzmann, R.; Albinati, A. Organometallics 1995, 14, 3311.
53. Note that for a given backbone chirality, the δ/λ-conformations alternate in going from a seven-membered to a nine-membered chelate. Thus (R)-BINAP-metal chelates exhibit a λ-conformation and (R)-BINAPO-phosphinite complexes a δ-conformation. The same has been seen before in going from five- to seven-membered chelates. For a compilation, see ref 15. Seebach, D.; Plattner, D. A.; Beck, A. K.; Wang, Y. M.; Hunziker, D.; Petter, W. Helv. Chim. Acta 1992, 75, 2171.
54. (a) Pregosin, P. S.; Salzmann, R. Coord. Chem. Rev. 1996, 115, 35.
55. (b) Pregosin, P. S.; Trabesinger, G. J. Chem. Soc., Dalton Trans. 1998, 727.
56. 9) using (S,S)-CHIRAPHOS as a ligand, we repeated the reaction (with diethyl malonate, the substrate under our study) and observed ee's of 75% (R) in THF at room temperature.
57. Rüegger, H.; Kunz, R. W.; Ammann, C. J.; Pregosin, P. S. Magn. Reson. Chem. 1991, 29, 197.
58. Pregosin, P. S.; Rüegger, H.; Salzmann, R.; Albinati, A.; Lianza, F.; Kunz, R. W. Organometallics 1994, 13, 5040.
59. Pregosin, P. S.; Rüegger, H.; Salzmann, R.; Albinati, A.; Lianza, F.; Kunz, R. W. Organometallics 1994, 13, 83.
60. Pregosin, P. S.; Salzmann, R.; Togni, A. Organometallics 1995, 14, 842.
61. Pregosin, P. S.; Salzmann, R. Magn. Reson. Chem. 1994, 32, 128.
62. Barbaro, P.; Currao, A.; Herrmann, J.; Nesper, R.; Pregosin, P. S.; Salzmann, R. Organometallics 1996, 15, 1879.
63. Boog-Wick, K.; Pregosin, P. S.; Trabesinger, G. Organometallics 1998, 17, 3254.
64. One intriguing possibility is that THF is involved in a π-σ-π equilibration process which renders the two phosphorus nuclei identical. Initial attack by THF will be followed by a rotation around a Pd-olefin complex, which has been identified as a viable intermediate by Reggellin and Helmchen in reactions of Pd-allyl complexes with nudeophiles. See ref 7d. equation presented
65. 2-symmetric nature of the ligand, the two (syn,syn) complexes derived from the two enantiomeric allyl acetates are identical.
66. Ammann, C. J.; Pregosin, P. S.; Rüegger, H.; Albinati, A.; Lianza, F.; Kunz, R. W. J. Organomet. Chem. 1992, 423, 415.
67. 42 has been labeled "suspect".
68. For an example of what appears to be a steric acceleration of a Pd-C bond cleavage in an allyl complex, see: Breutel, C.; Pregosin, P. S.; Salzmann, R.; Togni, A. J. Am. Chem. Soc. 1994, 116, 4067.
69. Still, W. C.; Kahn, M.; Mitra, A. J. Org. Chem. 1978, 43, 2923.
70. Mash, E. A.; Nelson, K. A.; Van Deusen, S.; Hemperly, S. B. Org. Synth. 1989, 68, 92.
71. Unruh, J. D.; Christenson, J. R. J. Mol. Catal. 1982, 14, 19.
72. Perich, J. W.; Johns, R. B. Synthesis 1988, 142.
73. Auburn, P. R.; Mackenzie, P. B.; Bosnich, B. J. Am. Chem. Soc. 1985, 107, 2033.