Ligand substituent effects on asymmetric induction. Effect of structural variations of the DIOP ligand on the Rh-catalyzed asymmetric hydrogenation of enamides

Organic Letters

Volumn 2, Issue 26, 2000, Pages 4137-4140

  Yan, Yuan Yong ^a   RajanBabu, T V ^a  

^a OHIO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0005746430     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol006591f     Document Type: Article

References (38)

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3. (c) Takaya, H.; Ohta, T.; Noyori, R. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH Publishers: New York, 1993; p i.,
4. (a) Pfaltz, A.; Lautens, M. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, 1999; p 833.
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6. Shimizu, K. D.; Snapper, M. L.; Hoveyda, A. H. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, 1999; p 1389. Burgess, K.; Porte, A. M. In Advances in Catalytic Processes; Doyle, M., Ed.; JAI Press: Greenwich, 1998; p 69.
7. Shimizu, K. D.; Snapper, M. L.; Hoveyda, A. H. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, 1999; p 1389. Burgess, K.; Porte, A. M. In Advances in Catalytic Processes; Doyle, M., Ed.; JAI Press: Greenwich, 1998; p 69.
8. For notable exceptions, see the following, (a) Salen complexes for epoxidation and epoxide opening reactions: Jaobsen, E. N.; Wu, M. H. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, 1999; p 649, 1309.
9. (b) Sugar phosphinite ligands for hydrocyanation and hydrogenation reactions: RajanBabu, T. V.; Casalnuovo, A. L.; Ayers, T. A. In Advances in Catalytic Processes; Doyle, M., Ed.; JAI Press: Greenwich, 1998; p 1.
10. (a) Yan, Y.-Y.; RajanBabu, T. V. J. Org. Chem. 2000, 65, 900.
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14. (a) Burk, M. J.; Wang, Y.; M.; Lee, J. R. J. Am. Chem. Soc. 1996, 118, 5142, and references therein.
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20. Kagan, H. B.; Fiaud, J. C.; Hoornaert, C.; Meyer, D.; Poulin, J. C. Bull. Soc. Chim. Belg. 1979, 88, 923.
21. 7f The analytically pure 5 is a white solid.
22. We thank Dr. M. J. Burk (Chirotecch) for the gift of these alcohols.
23. 11b (a) Casalnuovo, A. L.; RajanBabu, T. V.; Ayers, T. A.; Warren, T. H. J. Am. Chem. Soc. 1994, 116, 9869.
24. (b) Casey, C. P.; Paulsen, E. L.; Beuttenmueller, W.; Proft, B. R.; Petrovich, L. M.; Matter, B. A.; Powell, D. R. J. Am. Chem. Soc. 1997, 119, 11817.
25. See Supporting Information for details of experimental procedure and full characterization of the compounds.
26. 2 and the mixture was vigorously stirred for 10 h. After removing the catalyst on a plug of silica gel, the ee's of the products were determined by chiral GC (Chirasil-L-Val on WCOT fused silica 25 m × 0.25 mm).
27. For other results, see: Sinou, D.; Kagan, H. B. J. Organomet. Chem. 1976, 114, 325, and ref 7f.
28. For Rh-catalyzed reactions, see: (a) Inoguchi, K.; Sakuraba, S.; Achiwa, K. Synlett 1992, 169.
29. (b) Schnyder, A.; Hintermann, L.; Togni, A. Angew. Chem., Int. Ed. Engl. 1995, 34, 931.
30. (c) RajanBabu, T. V.; Ayers, T. A.; Halliday, G. A.; You, K. K.; Calabrese, J. C. J. Org. Chem. 1997, 62, 6012.
31. (d) RajanBabu, T. V.; Radetich, B.; You, K. K.; Ayers, T. A.; Casalnuovo, A. L.; Calabrese, J. C. J. Org. Chem. 1999, 64, 3429.
32. Hydrocyanation reactions: Casalnuovo, A. L.; RajanBabu, T. V.; Ayers, T. A.; Warren, T. H. J. Am. Chem. Soc. 1994, 116, 9869.
33. Prepared according to the procedure described by Burk et al.: Burk, M. J.; Casy, G.; Johnson, N. B. J. Org. Chem. 1998, 63, 6084.
34. Landis, C. R.; Halpern, J. J. Am. Chem. Soc. 1987, 109, 1746. For a highly readable summary of the mechanism of Rh-catalyzed asymmetric hydrogenation, see: Brown, J. M. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, 1999; p 121.
35. Landis, C. R.; Halpern, J. J. Am. Chem. Soc. 1987, 109, 1746. For a highly readable summary of the mechanism of Rh-catalyzed asymmetric hydrogenation, see: Brown, J. M. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, 1999; p 121.
36. 18b (a) Knowles, W. S.; Vineyard, B. D.; Sabacky, M. J.; Stults, B. R. In Fundamental Research in Homogeneous Catalysis; Ishii, Y.; Tsutsui, Eds.; Plenum: New York; Vol. 3, p 537.
37. (b) Hodgson, M.; Parker, D.; Taylor, R. J.; Ferguson, G. Organometallics 1988, 7, 1761. For a discussion of a related conformational change due to an α-substituent in an aminophosphine ligand, see: Pavlov, V. A.; Klabunovskii, E. I.; Struchkov, Y. T.; Voloboev, A. A.; Yanovsky, A. I. J. Mol. Catal. 1988, 44, 217, especially pp 218-220.
38. (b) Hodgson, M.; Parker, D.; Taylor, R. J.; Ferguson, G. Organometallics 1988, 7, 1761. For a discussion of a related conformational change due to an α-substituent in an aminophosphine ligand, see: Pavlov, V. A.; Klabunovskii, E. I.; Struchkov, Y. T.; Voloboev, A. A.; Yanovsky, A. I. J. Mol. Catal. 1988, 44, 217, especially pp 218-220.