Planar - Chiral ferrocenes in asymmetric catalysis: The impact of stereochemically inhomogeneous ligands

Organic Letters

Volumn 1, Issue 3, 1999, Pages 491-493

  Bolm, Carsten ^a   Muñiz, Kilian ^a   Hildebrand, Jens P ^a  

^a RWTH AACHEN UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001173688     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol990683r     Document Type: Article

References (45)

1. (a) Kagan, H. B.; Riant O. In Advances in Asymmetric Synthesis; Hassner, A., Ed.; JAI Press: Greenwich, CT, 1997; Vol. 2, p 189.
2. (b) Richards, C. J.; Locke, A. J. Tetrahedron: Asymmetry 1998, 9, 2377.
3. (c) Togni, A. Angew. Chem. 1996, 108, 1581; Angew. Chem., Int. Ed. Engl. 1996, 35, 1475.
4. (c) Togni, A. Angew. Chem. 1996, 108, 1581; Angew. Chem., Int. Ed. Engl. 1996, 35, 1475.
5. (d) Ferrocenes; Hayashi, T., Togni, A., Eds.; VCH: Weinheim, 1995.
6. (a) Sammakia, T.; Latham, H. A.; Schaad, D. R. J. Org. Chem. 1995, 60, 10.
7. (b) Sammakia, T.; Latham, H. A. J. Org. Chem. 1995, 60, 6002.
8. (c) Sammakia, T.; Latham, H. A. J. Org. Chem. 1996, 61, 1629.
9. (a) Richards, C. J.; Damalidis, T.; Hibbs, D. E.; Hursthouse, M. B. Synlett 1995, 74.
10. (b) Richards, C. J.; Mulvaney, A. W. Tetrahedron: Asymmetry 1996, 7, 1419.
11. (a) Nishibayashi, Y.; Uemura, S. Synlett 1995, 79.
12. (b) Nishibayashi, Y.; Segawa, K.; Arikawa, Y.; Ohe, K.; Hidai, M.; Uemura, S. J. Organomet. Chem. 1997, 545-546, 381.
13. See also: Ahn, K. H.; Cho, C-W.; Baek, H.-H.; Park, J.; Lee, S. J. Org. Chem. 1996, 61, 4937.
14. Hydrosilylation: (a) Nishibayashi, Y.; Segawa, K.; Ohe, K.; Uemura, S. Organometallics 1995, 14, 5486.
15. (b) Nishibayashi, Y.; Segawa, K.; Takada, H.; Ohe, K.; Uemura, S. Chem. Commun. 1996, 847.
16. Transfer hydrogenation: (a) Sammakia, T.; Stangeland, E. L. J. Org. Chem. 1997, 62, 6104.
17. (b) Nishibayashi, Y.; Takei, I.; Uemura, S.; Hidai, M. Organometallics 1998, 17, 3420.
18. (c) Arikawa, Y.; Ueoka, M.; Matoba, K.; Nishibayashi, Y.; Hidai, M.; Uemura, S. J. Organomet. Chem. 1999, 572, 163.
19. Allylic substitution: (a) Ahn, K. H.; Cho, C.-W.; Park, J.; Lee, S. Tetrahedron: Asymmetry 1997, 8, 1179.
20. (b) Ahn, K. H.; Cho, C.-W.; Park, J.; Lee, S. Bull. Korean Chem. Soc. 1997, 18, 789.
21. (c) For the importance of planar chirality in this reaction, see: You, S.-L.; Zhou, Y.-G.; Dai, L.-X. Chem. Commun. 1998, 2765.
22. Michael addition: Stangeland, E. L.; Sammakia, T. Tetrahedron 1997, 53, 16503.
23. Grignard cross-coupling: Richards, C. J.; Hibbs, D. E.; Hursthouse, M. B. Tetrahedron Lett. 1995, 36, 3745.
24. Asymmetric rearrangement of allylic imidates: Donde, Y.; Overman, L. E. J. Am. Chem. Soc. 1999, 121, 2933.
25. Bolm, C.; Muñiz-Fernández, K.; Seger, A.; Raabe, G. Synlett 1997, 1051.
26. Bolm, C.; Muñiz-Fernández, K.; Seger, A.; Raabe, G.; Günther, K. J. Org. Chem. 1998, 63, 7860.
27. Muñiz-Fernández, K. Ph.D. Thesis, RWTH Aachen 1998.
28. (a) Noyori, R.; Kitamura, M. Angew. Chem. 1991, 102, 34; Angew. Chem., Int. Ed. Engl. 1991, 30, 49.
29. (a) Noyori, R.; Kitamura, M. Angew. Chem. 1991, 102, 34; Angew. Chem., Int. Ed. Engl. 1991, 30, 49.
30. (b) Soai, K.; Niwa, S. Chem. Rev. 1992, 92, 833.
31. (a) Girard, C.; Kagan, H. B. Angew. Chem. 1998, 110, 3088; Angew. Chem., Int. Ed. Engl. 1998, 37, 2922.
32. (a) Girard, C.; Kagan, H. B. Angew. Chem. 1998, 110, 3088; Angew. Chem., Int. Ed. Engl. 1998, 37, 2922.
33. (b) Bolm, C. In Avanced Asymmetric Synthesis; Stephenson, R., Ed.; Capman and Hall: London, 1996; p 9.
34. (c) Avalos, M.; Babiano, R.; Ciutas, P.; Jiménez, J. L.; Palacios, J. C. Tetrahedron: Asymmetry 1997, 8, 2997.
35. Kitamura, M.; Yamakawa, M.; Oka, H.; Suga, H.; Noyori, R. Chem. Eur. J. 1996, 2, 1173 and references therein.
36. To date, there is only one report on a NLE for a ferrocene ligand in an asymmetric diethylzinc addition: Nicolosi, G.; Patti, A.; Morrone, R.; Piattelli, M. Tetrahedron: Asymmetry 1994, 5, 1639.
37. For kinetic implication of nonlinear effects see: (a) Blackmond, D. G. J. Am. Chem. Soc. 1998, 120, 13349.
38. (b) Blackmond, D. G., J. Am. Chem. Soc. 1997, 119, 12934.
39. (a) Kitamura, M.; Suga, S.; Niwa, M.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 4832.
40. Zhang, S. Y.; Girard, C.; Kagan, H. B. Tetrahedron: Asymmetry 1995, 6, 2637.
41. For other related investigations on diastereomeric catalyst mixtures see: (a) Corey, E. J.; Noe, M. C. J. Am. Chem. Soc. 1993, 115, 12579.
42. (b) Giardello M. A.; Conticello, V. P.; Brard, L.; Gagné, M. R., Marks, T. J. J. Am. Chem. Soc. 1994, 116, 10241.
43. (c) Fu, P.-F.; Brard, L.; Li, Y.; Marks, T. J. J. Am. Chem. Soc. 1995, 117, 7157.
44. For a recent report of an unselective ortho functionalization on 2-cymantrenyloxazolines, see: Kudis, S.; Helmchen, G. Angew. Chem. 1998, 110, 3210; Angew. Chem., Int. Ed. Engl. 1998, 37, 3047.
45. For a recent report of an unselective ortho functionalization on 2-cymantrenyloxazolines, see: Kudis, S.; Helmchen, G. Angew. Chem. 1998, 110, 3210; Angew. Chem., Int. Ed. Engl. 1998, 37, 3047.