Asymmetric palladium-catalyzed allylic alkylation using bis(oxazoline) ligands: Phenomenal reversal of enantioselectivity with a single chiral backbone

Organometallics

Volumn 18, Issue 23, 1999, Pages 4718-4723

  Hoarau, Olivier ^a   Aït Haddou, Hassan ^a   Daran, Jean Claude ^a   Cramailère, Dimitri ^a   Balavoine, Gilbert G A ^a  

^a LCC LABORATOIRE DE CHIMIE DE COORDINATION   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001474794     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om990437j     Document Type: Article

References (43)

1. (a) Hayashi, T. In Catalytic Asymmetrie Synthesis, Ojima, I., Ed.; VCH: Weinheim, New York, 1993; pp 325.
2. (b) Reiser, O. Angew. Chem., Int. Ed. Engl. 1993, 32, 547.
3. (c) Frost, C. G.; Howarth, J.; Williams, J. M. J. Tetrahedron Lett. 1992, 3, 1089.
4. (d) Trost, B. M.; van Vranken, D. L. Chem. Rev. 1996, 96, 395.
5. (a) Müller, D.; Umbricht, U.; Weber, B.; Pfaltz, A. Helv. Chim. Acta 1991, 74, 232.
6. (b) Leutenegger, U.; Umbricht, G.; Fahrni, C.; von Matt, P.; Pfaltz, A. Tetrahedron 1992, 48, 2143.
7. (c) Pfaltz, A. Acc. Chem. Res. 1993, 26, 339.
8. (d) Kubota, H.; Nakajima, M.; Koga, K, Tetrahedron Lett. 1993, 34, 8135.
9. (e) Tanner, D.; Anderson, P. G.; Harden, A.; Somfai, P. Tetrahedron Lett. 1994, 35, 4631.
10. (f) Kang, J.; Cho, W. O.; Cho, H. G. Tetrahydron: Asymmetry 1994, 5, 1347.
11. 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; see also ref 2d.
12. (a) Nordström, K.; Macedo, E.; Moberg, C. J. Org. Chem. 1997, 62, 1604.
13. (b) Bremberg, U.; Rahm, F.; Moberg, C. Tetrahedron: Asymmetry 1998, 9, 3437.
14. For the recent use of the bis(oxazoline) ligands in the asymmetric catalysis see: (a) Evans, D. A.; Kozlowski, M. C.; Murry, J. A.; Burgey, C. S.; Campos, K. R.; Connell, B. T.; Staples, R. J. J. Am. Chem. Soc. 1999, 121, 669. (b) Evans, D. A.; Burgey, C. S.; Kozlowski, M. C.; Tregay, S. W. J. Am. Chem. Soc. 1999, 121, 686. (c) Ghosh, A. K.; Mathivanan, P.; Cappiello, J. Tetrahedron: Asymmetry 1998, 9, 1-45. (d) Yao, S.; Johannsen, M.; Audrain, H.; Hazell, R. G.; Jørgensen, K. A. J. Am. Chem. Soc. 1998, 120, 8599. (e) Yao, S.; Johannsen, M.; Audrain, H.; Hazell, R. G.; Jørgensen, K. A. Angew. Chem. Int. Ed. Engl. 1998, 37, 3121. (f) Schulze, V.; Hoffmann, R. W. Chem. Eur. J. 1999, 5, 337.
15. For the recent use of the bis(oxazoline) ligands in the asymmetric catalysis see: (a) Evans, D. A.; Kozlowski, M. C.; Murry, J. A.; Burgey, C. S.; Campos, K. R.; Connell, B. T.; Staples, R. J. J. Am. Chem. Soc. 1999, 121, 669. (b) Evans, D. A.; Burgey, C. S.; Kozlowski, M. C.; Tregay, S. W. J. Am. Chem. Soc. 1999, 121, 686. (c) Ghosh, A. K.; Mathivanan, P.; Cappiello, J. Tetrahedron: Asymmetry 1998, 9, 1-45. (d) Yao, S.; Johannsen, M.; Audrain, H.; Hazell, R. G.; Jørgensen, K. A. J. Am. Chem. Soc. 1998, 120, 8599. (e) Yao, S.; Johannsen, M.; Audrain, H.; Hazell, R. G.; Jørgensen, K. A. Angew. Chem. Int. Ed. Engl. 1998, 37, 3121. (f) Schulze, V.; Hoffmann, R. W. Chem. Eur. J. 1999, 5, 337.
16. For the recent use of the bis(oxazoline) ligands in the asymmetric catalysis see: (a) Evans, D. A.; Kozlowski, M. C.; Murry, J. A.; Burgey, C. S.; Campos, K. R.; Connell, B. T.; Staples, R. J. J. Am. Chem. Soc. 1999, 121, 669. (b) Evans, D. A.; Burgey, C. S.; Kozlowski, M. C.; Tregay, S. W. J. Am. Chem. Soc. 1999, 121, 686. (c) Ghosh, A. K.; Mathivanan, P.; Cappiello, J. Tetrahedron: Asymmetry 1998, 9, 1-45. (d) Yao, S.; Johannsen, M.; Audrain, H.; Hazell, R. G.; Jørgensen, K. A. J. Am. Chem. Soc. 1998, 120, 8599. (e) Yao, S.; Johannsen, M.; Audrain, H.; Hazell, R. G.; Jørgensen, K. A. Angew. Chem. Int. Ed. Engl. 1998, 37, 3121. (f) Schulze, V.; Hoffmann, R. W. Chem. Eur. J. 1999, 5, 337.
17. For the recent use of the bis(oxazoline) ligands in the asymmetric catalysis see: (a) Evans, D. A.; Kozlowski, M. C.; Murry, J. A.; Burgey, C. S.; Campos, K. R.; Connell, B. T.; Staples, R. J. J. Am. Chem. Soc. 1999, 121, 669. (b) Evans, D. A.; Burgey, C. S.; Kozlowski, M. C.; Tregay, S. W. J. Am. Chem. Soc. 1999, 121, 686. (c) Ghosh, A. K.; Mathivanan, P.; Cappiello, J. Tetrahedron: Asymmetry 1998, 9, 1-45. (d) Yao, S.; Johannsen, M.; Audrain, H.; Hazell, R. G.; Jørgensen, K. A. J. Am. Chem. Soc. 1998, 120, 8599. (e) Yao, S.; Johannsen, M.; Audrain, H.; Hazell, R. G.; Jørgensen, K. A. Angew. Chem. Int. Ed. Engl. 1998, 37, 3121. (f) Schulze, V.; Hoffmann, R. W. Chem. Eur. J. 1999, 5, 337.
18. For the recent use of the bis(oxazoline) ligands in the asymmetric catalysis see: (a) Evans, D. A.; Kozlowski, M. C.; Murry, J. A.; Burgey, C. S.; Campos, K. R.; Connell, B. T.; Staples, R. J. J. Am. Chem. Soc. 1999, 121, 669. (b) Evans, D. A.; Burgey, C. S.; Kozlowski, M. C.; Tregay, S. W. J. Am. Chem. Soc. 1999, 121, 686. (c) Ghosh, A. K.; Mathivanan, P.; Cappiello, J. Tetrahedron: Asymmetry 1998, 9, 1-45. (d) Yao, S.; Johannsen, M.; Audrain, H.; Hazell, R. G.; Jørgensen, K. A. J. Am. Chem. Soc. 1998, 120, 8599. (e) Yao, S.; Johannsen, M.; Audrain, H.; Hazell, R. G.; Jørgensen, K. A. Angew. Chem. Int. Ed. Engl. 1998, 37, 3121. (f) Schulze, V.; Hoffmann, R. W. Chem. Eur. J. 1999, 5, 337.
19. For the recent use of the bis(oxazoline) ligands in the asymmetric catalysis see: (a) Evans, D. A.; Kozlowski, M. C.; Murry, J. A.; Burgey, C. S.; Campos, K. R.; Connell, B. T.; Staples, R. J. J. Am. Chem. Soc. 1999, 121, 669. (b) Evans, D. A.; Burgey, C. S.; Kozlowski, M. C.; Tregay, S. W. J. Am. Chem. Soc. 1999, 121, 686. (c) Ghosh, A. K.; Mathivanan, P.; Cappiello, J. Tetrahedron: Asymmetry 1998, 9, 1-45. (d) Yao, S.; Johannsen, M.; Audrain, H.; Hazell, R. G.; Jørgensen, K. A. J. Am. Chem. Soc. 1998, 120, 8599. (e) Yao, S.; Johannsen, M.; Audrain, H.; Hazell, R. G.; Jørgensen, K. A. Angew. Chem. Int. Ed. Engl. 1998, 37, 3121. (f) Schulze, V.; Hoffmann, R. W. Chem. Eur. J. 1999, 5, 337.
20. Hoarau, O.; Aït-Haddou, H.; Castro, M.; Balavoine, G. G. A. Tetrahedron: Asymmetry 1997, 8, 3755.
21. (a) Hayashi, T.; Yamamoto, A.; Hagihara, T.; Ito, Y. Tetrahedron Lett. 1986, 27, 191.
22. (b) von Matt, P.; Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 566.
23. Reversal in enantioselectivity with bis(oxazoline)-metal catalysts depending on the oxazoline ring substituent was very recently observed in other reactions see: (a) Evans, D. A.; Johnson, J. S.; Burgey, C. S.; Campos, K. R. Tetrahedron Lett. 1999, 40, 2879. (b) Johannsen, M.; Jørgensen, K. A. J. Org. Chem. 1995, 60, 5757. (c) Johannsen, M.; Yao, S.; Jørgensen, K. A. Chem. Commun. 1997, 2169. (d) Johannsen, M.; Yao, S.; Graven, A.; Jørgensen, K. A. Pure Appl. Chem. 1998, 70, 1117.
24. Reversal in enantioselectivity with bis(oxazoline)-metal catalysts depending on the oxazoline ring substituent was very recently observed in other reactions see: (a) Evans, D. A.; Johnson, J. S.; Burgey, C. S.; Campos, K. R. Tetrahedron Lett. 1999, 40, 2879. (b) Johannsen, M.; Jørgensen, K. A. J. Org. Chem. 1995, 60, 5757. (c) Johannsen, M.; Yao, S.; Jørgensen, K. A. Chem. Commun. 1997, 2169. (d) Johannsen, M.; Yao, S.; Graven, A.; Jørgensen, K. A. Pure Appl. Chem. 1998, 70, 1117.
25. Reversal in enantioselectivity with bis(oxazoline)-metal catalysts depending on the oxazoline ring substituent was very recently observed in other reactions see: (a) Evans, D. A.; Johnson, J. S.; Burgey, C. S.; Campos, K. R. Tetrahedron Lett. 1999, 40, 2879. (b) Johannsen, M.; Jørgensen, K. A. J. Org. Chem. 1995, 60, 5757. (c) Johannsen, M.; Yao, S.; Jørgensen, K. A. Chem. Commun. 1997, 2169. (d) Johannsen, M.; Yao, S.; Graven, A.; Jørgensen, K. A. Pure Appl. Chem. 1998, 70, 1117.
26. Reversal in enantioselectivity with bis(oxazoline)-metal catalysts depending on the oxazoline ring substituent was very recently observed in other reactions see: (a) Evans, D. A.; Johnson, J. S.; Burgey, C. S.; Campos, K. R. Tetrahedron Lett. 1999, 40, 2879. (b) Johannsen, M.; Jørgensen, K. A. J. Org. Chem. 1995, 60, 5757. (c) Johannsen, M.; Yao, S.; Jørgensen, K. A. Chem. Commun. 1997, 2169. (d) Johannsen, M.; Yao, S.; Graven, A.; Jørgensen, K. A. Pure Appl. Chem. 1998, 70, 1117.
27. Complete decomposition of the catalyst was observed when the dimethyl malonate anion was added.
28. (a) Sawamura, M.; Ito, Y. Chem. Rev. 1992, 92, 857.
29. (b) Hayashi, T.; Kanehira, K.; Hagihara, T.; Kumada, M. J. Org. Chem. 1988, 53, 113.
30. (c) Hayashi, T.; Yamamoto, A.; Ito, Y.; Nishioka, E.; Miura, H.; Yanagi, K. J. Am. Chem. Soc. 1989, 111, 6301.
31. (d) Yamazaki, A.; Morimoto, T.; Achiwa, K. Tetrahedron Lett. 1993, 4, 2287.
32. (a) Togni, A.; Burkhardt, U.; Gramlich, V.; Pregosin, P. S.; Salzman, R. J. Am. Chem. Soc. 1996, 118, 1031.
33. (b) Nomura, N.; Mermet-Bouvier, Y. C.; Rajanbabu, T. V. Synlett 1996, 745.
34. For the preparation of the (π-allyl)-palladium-ligand complexes 7 and 8 see: refs 9c and 3.
35. Zehnder, M.; von Matt, P.; Pfaltz, A. Acta Crystallogr., Sect. C 1995, 1109.
36. Hoarau, O.; Cramailère, D.; Aït-Haddou, H.; Pezet, F.; Daran, J.-C.; Balavoine, G. G. A. To be submitted.
37. For the preparation of the carbonate 1b see: Gais, H.-J.; Eichelmann, H.; Spalthoff, N.; Gerhards, F.; Frank, M.; Raabe, G. Tetrahydron: Asymmetry 1998, 9, 235.
38. 2 was prepared according to Bosnich's procedure; see: (a) Auburn, P. R.; Mackenzie, P. B.; Bosnich, B. J. Am. Chem. Soc. 1985, 107, 2033. (b) Mackenzie, P. B.; Whelan, J.; Bosnich, B. J. Am. Chem. Soc. 1985, 107, 2046.
39. 2 was prepared according to Bosnich's procedure; see: (a) Auburn, P. R.; Mackenzie, P. B.; Bosnich, B. J. Am. Chem. Soc. 1985, 107, 2033. (b) Mackenzie, P. B.; Whelan, J.; Bosnich, B. J. Am. Chem. Soc. 1985, 107, 2046.
40. Altomare, A.; Burla, M. C.; Camalli, M.; Cascarano, G.; Giacovazzo, C.; Guagliardi, A.; Poidori, G. SIR92 - a program for automatic solution of crystal structures by direct methods. J. Appl. Crystallogr. 1994, 27, 435.
41. Prince, E. Mathematical Techniques in Crystallography; Springer-Verlag: Berlin, 1982.
42. Watkin, D. J.; Prout, C. K.; Carruthers, J. R.; Betteridge, P. W. CRYSTALS Issue 10; Chemical Crystallography Laboratory: University of Oxford, Oxford, 1996.
43. Watkin, D. J.; Prout, C. K.; Pearce, L. J. CAMERON; Chemical Crystallography Laboratory: University of Oxford, Oxford, 1996.