Mixtures of chiral and achiral monodentate ligands in asymmetric Rh-catalyzed olefin hydrogenation: Reversal of enantioselectivity

Tetrahedron Letters

Volumn 44, Issue 24, 2003, Pages 4593-4596

  Reetz, Manfred T ^a   Mehler, Gerlinde ^a  

^a MAX PLANCK INSTITUT FÜR KOHLENFORSCHUNG   (Germany)

Author keywords

Asymmetric catalysis; Combinatorial chemistry; Hydrogenation; Phosphorus ligands; Rhodium

Indexed keywords

ALKENE; LIGAND; RHODIUM;

ARTICLE; CATALYSIS; CATALYST; CHIRALITY; COMBINATORIAL CHEMISTRY; ENANTIOSELECTIVITY; HYDROGENATION; RACEMIC MIXTURE;

EID: 0038065528     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00976-6     Document Type: Article

References (28)

1. Reetz, M. T.; Sell, T.; Meiswinkel, A.; Mehler, G. Angew. Chem. 2003, 115, 814-817; Angew. Chem., Int. Ed. 2003, 42, 790-793 Reetz, M. T.; Meiswinkel, A.; Sell, T.; Mehler, G. Patent Application DE-A 10247633.0 Sell, T. Dissertation, Ruhr-Universität Bochum, Germany, 2002.
2. Reetz M.T., Sell T. Tetrahedron Lett. 41:2000;6333-6336.
3. Claver C., Fernandez E., Gillon A., Heslop K., Hyett D.J., Martorell A., Orpen A.G., Pringle P.G. Chem. Commun. (Cambridge). 2000;961-962.
4. Reetz, M. T.; Mehler, G. Angew. Chem. 2000, 112, 4047-4049; Angew. Chem., Int. Ed. 2000, 39, 3889-3890.
5. Reetz, M. T.; Mehler, G. Angew. Chem. 2000, 112, 4047-4049; Angew. Chem., Int. Ed. 2000, 39, 3889-3890.
6. Further examples of this principle using mixtures of different monophosphoramidites have since been observed by B. Feringa (private communication) to be published in Org. Biomol. Chem.
7. Reetz, M. T.; Neugebauer, T. Angew. Chem. 1999, 111, 134-137; Angew. Chem., Int. Ed. 1999, 38, 179-181 Blackmond, D. G.; Rosner, T.; Neugebauer, T.; Reetz, M. T. Angew. Chem. 1999, 111, 2333-2335; Angew. Chem., Int. Ed. 1999, 38, 2196-2199.
8. We thank Professor B. Breit (Universität Freiburg) for a sample of compound 14 .
9. van den Berg M., Minnaard A.J., Schudde E.P., van Esch J., de Vries A.H.M., de Vries J.G., Feringa B.L. J. Am. Chem. Soc. 122:2000;11539-11540.
10. Minnaard A.J., van den Berg M., Schudde E.P., van Esch J., de Vries A.H.M., de Vries J.G., Feringa B.L. Chim. Oggi. 19:2001;12-13.
11. Preliminary hydrogenation experiments using the β-phenyl analog of 1 leading to the phenylalanine derivative show a similar trend. For example, upon using 4b / 9 reversal of enantioselectivity is observed (ee=20.5% (R) versus ee=82.8% (S) employing 4b alone).
12. Our approaches are different from the principle of self-organization of catalysts as for example in the case of Ti-catalysts formed from two different chiral diols used in carbonyl ene-reactions, or the principle of selective activation of racemic catalysts, both described by the pioneering work of Mikami. See: (a) Mikami, K.; Matsukawa, S.; Volk, T.; Terada, M. Angew. Chem. 1997, 109, 2936-2939; Angew. Chem., Int. Ed. Engl. 1997, 36, 2768-2771; (b) Mikami, K.; Matsukawa, S. Nature 1997, 385, 613-615.
13. Our approaches are different from the principle of self-organization of catalysts as for example in the case of Ti-catalysts formed from two different chiral diols used in carbonyl ene-reactions, or the principle of selective activation of racemic catalysts, both described by the pioneering work of Mikami. See: (a) Mikami, K.; Matsukawa, S.; Volk, T.; Terada, M. Angew. Chem. 1997, 109, 2936-2939; Angew. Chem., Int. Ed. Engl. 1997, 36, 2768-2771; (b) Mikami, K.; Matsukawa, S. Nature 1997, 385, 613-615.
14. Our approaches are different from the principle of self-organization of catalysts as for example in the case of Ti-catalysts formed from two different chiral diols used in carbonyl ene-reactions, or the principle of selective activation of racemic catalysts, both described by the pioneering work of Mikami. See: (a) Mikami, K.; Matsukawa, S.; Volk, T.; Terada, M. Angew. Chem. 1997, 109, 2936-2939; Angew. Chem., Int. Ed. Engl. 1997, 36, 2768-2771; (b) Mikami, K.; Matsukawa, S. Nature 1997, 385, 613-615.
15. For key publications of combinatorial asymmetric catalysis, see: (a) Francis, M. B.; Jacobsen, E. N. Angew. Chem. 1999, 111, 987-991; Angew. Chem., Int. Ed. 1999, 38, 937-941; (b) Gilbertson, S. R.; Chang, C.-W. T. Chem. Commun. (Cambridge) 1997, 975-976; (c) Gennari, C.; Ceccarelli, S.; Piarulli, U.; Montalbetti, C. A. G. N.; Jackson, R. F. W. J. Org. Chem. 1998, 63, 5312-5313; (d) Burgess, K.; Lim, H.-J.; Porte, A. M.; Sulikowski, G. A. Angew. Chem. 1996, 108, 192-194; Angew. Chem., Int. Ed. Engl. 1996, 35, 220-222; (e) Krueger, C. A.; Kuntz, K. W.; Dzierba, C. D.; Wirschun, W. G.; Gleason, J. D.; Snapper, M. L.; Hoveyda, A. H. J. Am. Chem. Soc. 1999, 121, 4284-4285; (f) Long, J.; Hu, J.; Shen, X.; Ji, B.; Ding, K. J. Am. Chem. Soc. 2002, 124, 10-11; (g) Berkessel, A.; Riedl, R. J. Comb. Chem. 2000, 2, 215-219; (h) Dahmen, S.; Bräse, S. Synthesis 2001, 1431-1449.
16. For key publications of combinatorial asymmetric catalysis, see: (a) Francis, M. B.; Jacobsen, E. N. Angew. Chem. 1999, 111, 987-991; Angew. Chem., Int. Ed. 1999, 38, 937-941; (b) Gilbertson, S. R.; Chang, C.-W. T. Chem. Commun. (Cambridge) 1997, 975-976; (c) Gennari, C.; Ceccarelli, S.; Piarulli, U.; Montalbetti, C. A. G. N.; Jackson, R. F. W. J. Org. Chem. 1998, 63, 5312-5313; (d) Burgess, K.; Lim, H.-J.; Porte, A. M.; Sulikowski, G. A. Angew. Chem. 1996, 108, 192-194; Angew. Chem., Int. Ed. Engl. 1996, 35, 220-222; (e) Krueger, C. A.; Kuntz, K. W.; Dzierba, C. D.; Wirschun, W. G.; Gleason, J. D.; Snapper, M. L.; Hoveyda, A. H. J. Am. Chem. Soc. 1999, 121, 4284-4285; (f) Long, J.; Hu, J.; Shen, X.; Ji, B.; Ding, K. J. Am. Chem. Soc. 2002, 124, 10-11; (g) Berkessel, A.; Riedl, R. J. Comb. Chem. 2000, 2, 215-219; (h) Dahmen, S.; Bräse, S. Synthesis 2001, 1431-1449.
17. For key publications of combinatorial asymmetric catalysis, see: (a) Francis, M. B.; Jacobsen, E. N. Angew. Chem. 1999, 111, 987-991; Angew. Chem., Int. Ed. 1999, 38, 937-941; (b) Gilbertson, S. R.; Chang, C.-W. T. Chem. Commun. (Cambridge) 1997, 975-976; (c) Gennari, C.; Ceccarelli, S.; Piarulli, U.; Montalbetti, C. A. G. N.; Jackson, R. F. W. J. Org. Chem. 1998, 63, 5312-5313; (d) Burgess, K.; Lim, H.-J.; Porte, A. M.; Sulikowski, G. A. Angew. Chem. 1996, 108, 192-194; Angew. Chem., Int. Ed. Engl. 1996, 35, 220-222; (e) Krueger, C. A.; Kuntz, K. W.; Dzierba, C. D.; Wirschun, W. G.; Gleason, J. D.; Snapper, M. L.; Hoveyda, A. H. J. Am. Chem. Soc. 1999, 121, 4284-4285; (f) Long, J.; Hu, J.; Shen, X.; Ji, B.; Ding, K. J. Am. Chem. Soc. 2002, 124, 10-11; (g) Berkessel, A.; Riedl, R. J. Comb. Chem. 2000, 2, 215-219; (h) Dahmen, S.; Bräse, S. Synthesis 2001, 1431-1449.
18. For key publications of combinatorial asymmetric catalysis, see: (a) Francis, M. B.; Jacobsen, E. N. Angew. Chem. 1999, 111, 987-991; Angew. Chem., Int. Ed. 1999, 38, 937-941; (b) Gilbertson, S. R.; Chang, C.-W. T. Chem. Commun. (Cambridge) 1997, 975-976; (c) Gennari, C.; Ceccarelli, S.; Piarulli, U.; Montalbetti, C. A. G. N.; Jackson, R. F. W. J. Org. Chem. 1998, 63, 5312-5313; (d) Burgess, K.; Lim, H.-J.; Porte, A. M.; Sulikowski, G. A. Angew. Chem. 1996, 108, 192-194; Angew. Chem., Int. Ed. Engl. 1996, 35, 220-222; (e) Krueger, C. A.; Kuntz, K. W.; Dzierba, C. D.; Wirschun, W. G.; Gleason, J. D.; Snapper, M. L.; Hoveyda, A. H. J. Am. Chem. Soc. 1999, 121, 4284-4285; (f) Long, J.; Hu, J.; Shen, X.; Ji, B.; Ding, K. J. Am. Chem. Soc. 2002, 124, 10-11; (g) Berkessel, A.; Riedl, R. J. Comb. Chem. 2000, 2, 215-219; (h) Dahmen, S.; Bräse, S. Synthesis 2001, 1431-1449.
19. For key publications of combinatorial asymmetric catalysis, see: (a) Francis, M. B.; Jacobsen, E. N. Angew. Chem. 1999, 111, 987-991; Angew. Chem., Int. Ed. 1999, 38, 937-941; (b) Gilbertson, S. R.; Chang, C.-W. T. Chem. Commun. (Cambridge) 1997, 975-976; (c) Gennari, C.; Ceccarelli, S.; Piarulli, U.; Montalbetti, C. A. G. N.; Jackson, R. F. W. J. Org. Chem. 1998, 63, 5312-5313; (d) Burgess, K.; Lim, H.-J.; Porte, A. M.; Sulikowski, G. A. Angew. Chem. 1996, 108, 192-194; Angew. Chem., Int. Ed. Engl. 1996, 35, 220-222; (e) Krueger, C. A.; Kuntz, K. W.; Dzierba, C. D.; Wirschun, W. G.; Gleason, J. D.; Snapper, M. L.; Hoveyda, A. H. J. Am. Chem. Soc. 1999, 121, 4284-4285; (f) Long, J.; Hu, J.; Shen, X.; Ji, B.; Ding, K. J. Am. Chem. Soc. 2002, 124, 10-11; (g) Berkessel, A.; Riedl, R. J. Comb. Chem. 2000, 2, 215-219; (h) Dahmen, S.; Bräse, S. Synthesis 2001, 1431-1449.
20. For key publications of combinatorial asymmetric catalysis, see: (a) Francis, M. B.; Jacobsen, E. N. Angew. Chem. 1999, 111, 987-991; Angew. Chem., Int. Ed. 1999, 38, 937-941; (b) Gilbertson, S. R.; Chang, C.-W. T. Chem. Commun. (Cambridge) 1997, 975-976; (c) Gennari, C.; Ceccarelli, S.; Piarulli, U.; Montalbetti, C. A. G. N.; Jackson, R. F. W. J. Org. Chem. 1998, 63, 5312-5313; (d) Burgess, K.; Lim, H.-J.; Porte, A. M.; Sulikowski, G. A. Angew. Chem. 1996, 108, 192-194; Angew. Chem., Int. Ed. Engl. 1996, 35, 220-222; (e) Krueger, C. A.; Kuntz, K. W.; Dzierba, C. D.; Wirschun, W. G.; Gleason, J. D.; Snapper, M. L.; Hoveyda, A. H. J. Am. Chem. Soc. 1999, 121, 4284-4285; (f) Long, J.; Hu, J.; Shen, X.; Ji, B.; Ding, K. J. Am. Chem. Soc. 2002, 124, 10-11; (g) Berkessel, A.; Riedl, R. J. Comb. Chem. 2000, 2, 215-219; (h) Dahmen, S.; Bräse, S. Synthesis 2001, 1431-1449.
21. For key publications of combinatorial asymmetric catalysis, see: (a) Francis, M. B.; Jacobsen, E. N. Angew. Chem. 1999, 111, 987-991; Angew. Chem., Int. Ed. 1999, 38, 937-941; (b) Gilbertson, S. R.; Chang, C.-W. T. Chem. Commun. (Cambridge) 1997, 975-976; (c) Gennari, C.; Ceccarelli, S.; Piarulli, U.; Montalbetti, C. A. G. N.; Jackson, R. F. W. J. Org. Chem. 1998, 63, 5312-5313; (d) Burgess, K.; Lim, H.-J.; Porte, A. M.; Sulikowski, G. A. Angew. Chem. 1996, 108, 192-194; Angew. Chem., Int. Ed. Engl. 1996, 35, 220-222; (e) Krueger, C. A.; Kuntz, K. W.; Dzierba, C. D.; Wirschun, W. G.; Gleason, J. D.; Snapper, M. L.; Hoveyda, A. H. J. Am. Chem. Soc. 1999, 121, 4284-4285; (f) Long, J.; Hu, J.; Shen, X.; Ji, B.; Ding, K. J. Am. Chem. Soc. 2002, 124, 10-11; (g) Berkessel, A.; Riedl, R. J. Comb. Chem. 2000, 2, 215-219; (h) Dahmen, S.; Bräse, S. Synthesis 2001, 1431-1449.
22. For key publications of combinatorial asymmetric catalysis, see: (a) Francis, M. B.; Jacobsen, E. N. Angew. Chem. 1999, 111, 987-991; Angew. Chem., Int. Ed. 1999, 38, 937-941; (b) Gilbertson, S. R.; Chang, C.-W. T. Chem. Commun. (Cambridge) 1997, 975-976; (c) Gennari, C.; Ceccarelli, S.; Piarulli, U.; Montalbetti, C. A. G. N.; Jackson, R. F. W. J. Org. Chem. 1998, 63, 5312-5313; (d) Burgess, K.; Lim, H.-J.; Porte, A. M.; Sulikowski, G. A. Angew. Chem. 1996, 108, 192-194; Angew. Chem., Int. Ed. Engl. 1996, 35, 220-222; (e) Krueger, C. A.; Kuntz, K. W.; Dzierba, C. D.; Wirschun, W. G.; Gleason, J. D.; Snapper, M. L.; Hoveyda, A. H. J. Am. Chem. Soc. 1999, 121, 4284-4285; (f) Long, J.; Hu, J.; Shen, X.; Ji, B.; Ding, K. J. Am. Chem. Soc. 2002, 124, 10-11; (g) Berkessel, A.; Riedl, R. J. Comb. Chem. 2000, 2, 215-219; (h) Dahmen, S.; Bräse, S. Synthesis 2001, 1431-1449.
23. For key publications of combinatorial asymmetric catalysis, see: (a) Francis, M. B.; Jacobsen, E. N. Angew. Chem. 1999, 111, 987-991; Angew. Chem., Int. Ed. 1999, 38, 937-941; (b) Gilbertson, S. R.; Chang, C.-W. T. Chem. Commun. (Cambridge) 1997, 975-976; (c) Gennari, C.; Ceccarelli, S.; Piarulli, U.; Montalbetti, C. A. G. N.; Jackson, R. F. W. J. Org. Chem. 1998, 63, 5312-5313; (d) Burgess, K.; Lim, H.-J.; Porte, A. M.; Sulikowski, G. A. Angew. Chem. 1996, 108, 192-194; Angew. Chem., Int. Ed. Engl. 1996, 35, 220-222; (e) Krueger, C. A.; Kuntz, K. W.; Dzierba, C. D.; Wirschun, W. G.; Gleason, J. D.; Snapper, M. L.; Hoveyda, A. H. J. Am. Chem. Soc. 1999, 121, 4284-4285; (f) Long, J.; Hu, J.; Shen, X.; Ji, B.; Ding, K. J. Am. Chem. Soc. 2002, 124, 10-11; (g) Berkessel, A.; Riedl, R. J. Comb. Chem. 2000, 2, 215-219; (h) Dahmen, S.; Bräse, S. Synthesis 2001, 1431-1449.
24. For key publications of combinatorial asymmetric catalysis, see: (a) Francis, M. B.; Jacobsen, E. N. Angew. Chem. 1999, 111, 987-991; Angew. Chem., Int. Ed. 1999, 38, 937-941; (b) Gilbertson, S. R.; Chang, C.-W. T. Chem. Commun. (Cambridge) 1997, 975-976; (c) Gennari, C.; Ceccarelli, S.; Piarulli, U.; Montalbetti, C. A. G. N.; Jackson, R. F. W. J. Org. Chem. 1998, 63, 5312-5313; (d) Burgess, K.; Lim, H.-J.; Porte, A. M.; Sulikowski, G. A. Angew. Chem. 1996, 108, 192-194; Angew. Chem., Int. Ed. Engl. 1996, 35, 220-222; (e) Krueger, C. A.; Kuntz, K. W.; Dzierba, C. D.; Wirschun, W. G.; Gleason, J. D.; Snapper, M. L.; Hoveyda, A. H. J. Am. Chem. Soc. 1999, 121, 4284-4285; (f) Long, J.; Hu, J.; Shen, X.; Ji, B.; Ding, K. J. Am. Chem. Soc. 2002, 124, 10-11; (g) Berkessel, A.; Riedl, R. J. Comb. Chem. 2000, 2, 215-219; (h) Dahmen, S.; Bräse, S. Synthesis 2001, 1431-1449.
25. For reviews of combinatorial and evolutionary methods for the generation of enantioselective (bio)catalysts as well as high-throughput screening systems, see: (a) Reetz, M. T. Angew. Chem. 2001, 113, 292-320; Angew. Chem., Int. Ed. 2001, 40, 284-310; (b) Reetz, M. T. Angew. Chem. 2002, 114, 1391-1394; Angew. Chem.,
26. For reviews of combinatorial and evolutionary methods for the generation of enantioselective (bio)catalysts as well as high-throughput screening systems, see: (a) Reetz, M. T. Angew. Chem. 2001, 113, 292-320; Angew. Chem., Int. Ed. 2001, 40, 284-310;
27. For reviews of combinatorial and evolutionary methods for the generation of enantioselective (bio)catalysts as well as high-throughput screening systems, see: (a) Reetz, M. T. Angew. Chem. 2001, 113, 292-320; Angew. Chem., Int. Ed. 2001, 40, 284-310;
28. For reviews of combinatorial and evolutionary methods for the generation of enantioselective (bio)catalysts as well as high-throughput screening systems, see: (a) Reetz, M. T. Angew. Chem. 2001, 113, 292-320; Angew. Chem., Int. Ed. 2001, 40, 284-310; (b) Reetz, M. T. Angew. Chem. 2002, 114, 1391-1394; Angew. Chem., Int. Ed. 2002, 41, 1335-1338.