Unprecedented Electronic and Steric Effects in Palladium-Catalyzed Asymmetric Allylation: Switching of Enantioselectivity with a Single Chiral Backbone

Synlett

Volumn 1996, Issue 8, 1996, Pages 745-746

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

^a OHIO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002560434     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5534     Document Type: Article

References (29)

1. Recent reviews: a) Frost, C. G.; Howarth, J.; Williams, J. M. J. Tetrahedron: Asymmetry 1992, 3, 1089. b) Hayashi, T. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH, New York, 1993, p.325; c) Trost, B. M.; Vranken, D. L. V. Chem. Rev. 1996, 96, 395.
2. Recent reviews: a) Frost, C. G.; Howarth, J.; Williams, J. M. J. Tetrahedron: Asymmetry 1992, 3, 1089. b) Hayashi, T. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH, New York, 1993, p.325; c) Trost, B. M.; Vranken, D. L. V. Chem. Rev. 1996, 96, 395.
3. Recent reviews: a) Frost, C. G.; Howarth, J.; Williams, J. M. J. Tetrahedron: Asymmetry 1992, 3, 1089. b) Hayashi, T. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH, New York, 1993, p.325; c) Trost, B. M.; Vranken, D. L. V. Chem. Rev. 1996, 96, 395.
4. a) von Matt, P.; Lloyd-Jones, G. C.; Minidis, A. B. E.; Pfaltz, A.; Macko, L; Neuburger, M.; Zehnder, M.; Rüegger, H.; Pregosin, P. S. Helv. Chim. Acta 1995, 78, 265.
5. b) Andersson, P. G.; Harden, A.; Tanner, D.; Norrby, P. -O. Chem. Eur. J. 1995, 1, 12.
6. Kubota, H.; Nakajima, M.; Koga, K. Tetrahedron Lett. 1993, 34, 8135.
7. Allen, J. V.; Coote, S. J.; Dawson, G. J.; Frost, C. G.; Martin, C. J.; Williams, J. M. J. J. Chem. Soc., Perkin Trans. I 1994, 2065.
8. e) Sprinz, J.; Kiefer, M.; Helmchen, G.; Reggelin, M.; Huttner, G.; Walter, O.; Zsolnai, L. Tetrahedron Lett. 1994, 35, 1523.
9. f) Brown, J. M.; Hulmes, D. I.; Guiry, P. J. Tetrahedron, 1994, 50, 4493.
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11. h) Seebach, D; Devaquet, E.; Ernst, A.; Hayakawa, M.; Kühnle, F. N. M.; Schweizer, W. B.; Weber, B. Helv. Chim. Acta. 1995, 78, 1636.
12. a) Auburn, P. R.; Mackenzie, P. B.; Bosnich, B. J. Am. Chem. Soc. 1985, 107, 2033.
13. b) Mackenzie, P. B.; Whelan, J.; Bosnich, B. ibid, 1985, 107, 2046.
14. a) RajanBabu, T. V.; Casalnuovo, A. L. J. Am. Chem. Soc. 1992, 114, 6265.
15. b) idem, Pure Appl. Chem. 1994, 66, 1535.
16. Casalnuovo, A. L.; RajanBabu, T. V.; Ayers, T. A.; Warren, T. H. J. Am. Chem. Soc. 1994, 116, 9869.
17. RajanBabu, T. V.; Ayers, T. A.; Casalnuovo, A. L. J. Am. Chem. Soc. 1994, 116, 4101.
18. e) Selke, R.; Pracejus, H. J. Mol. Catal. 1986, 37, 213.
19. For leading references: Hydrocyanation: ref. 4c; Hydrogenation: Landis, C. R.; Halpern, J. J. Am. Chem. Soc. 1987, 109, 1746. Brown, J. M. Chem. Soc. Rev. 1993, 25 and references cited therein.
20. For leading references: Hydrocyanation: ref. 4c; Hydrogenation: Landis, C. R.; Halpern, J. J. Am. Chem. Soc. 1987, 109, 1746. Brown, J. M. Chem. Soc. Rev. 1993, 25 and references cited therein.
21. For effects of substituents in meta position of the aromatic phosphinite see: Trost, B. M.; Murphy, D. J. Organometallics, 1985, 4, 1143.
22. Trifluoromethyl substituent is roughly the same size as i-propyl.
23. Recently Achiwa et al. reported reversal of chirality induced by non-chiral substituents in asymmetric hydrogenation and allylic amination; Morimoto, T.; Nakajima, N.; Achiwa, K. Tetrahedron: Asymmetry 1995, 6, 23. Yamazaki, A.; Achiwa, A. ibid. 1995, 6, 51.
24. Recently Achiwa et al. reported reversal of chirality induced by non-chiral substituents in asymmetric hydrogenation and allylic amination; Morimoto, T.; Nakajima, N.; Achiwa, K. Tetrahedron: Asymmetry 1995, 6, 23. Yamazaki, A.; Achiwa, A. ibid. 1995, 6, 51.
25. As this manuscript was being prepared, Togni et al. reported the possibility with one ligand for the first time, where 5-a vs 6-c process might reverse the enantioselectivity due to a steric influence in allylic amination; Togni, A.; Burckhardt, U.; Gramlich, V.; Pregosin, P. S.; Salzmann, R. J. Am. Chem. Soc. 1996, 118, 1031.
26. a) Herrmann, J.; Pregosin, P. S.; Salzmann, R.; Albinati, A. Organometallics 1995, 14, 3311.
27. b) ref. 2e-f.
28. A remote substituent on the P-Ar group should have little electronic effect on the λ to δ conformational change in the 7-membered Pd-chelate. See: Pavlov, V. A.; Klabunovskii, E. I.; Struchkov, Y. T.; Voloboev, A. A.; Yanovsky, A. I. J. Mol. Catal. 1988, 44, 217. Toth, I.; Hanson, B. E. Organometallics, 1993, 12, 1506.
29. A remote substituent on the P-Ar group should have little electronic effect on the λ to δ conformational change in the 7-membered Pd-chelate. See: Pavlov, V. A.; Klabunovskii, E. I.; Struchkov, Y. T.; Voloboev, A. A.; Yanovsky, A. I. J. Mol. Catal. 1988, 44, 217. Toth, I.; Hanson, B. E. Organometallics, 1993, 12, 1506.