A new principle in combinatorial asymmetric transition-metal catalysis: Mixtures of chiral monodentate P ligands

Angewandte Chemie - International Edition

Volumn 42, Issue 7, 2003, Pages 790-793

  Reetz, Manfred T ^a   Sell, Thorsten ^a   Meiswinkel, Andreas ^a   Mehler, Gerlinde ^a  

^a MAX PLANCK INSTITUT FÜR KOHLENFORSCHUNG   (Germany)

Author keywords

Asymmetric catalysis; Combinatorial chemistry; Hydrogenation; Phosphorus; Rhodium

Indexed keywords

CATALYSIS; HYDROGENATION; PHOSPHATES; RHODIUM COMPOUNDS;

LIGANDS;

TRANSITION METAL ALLOYS;

1,5 CYCLOOCTADIENE; ALKADIENE; ALKENE; PHOSPHITE; PHOSPHORUS DERIVATIVE; RHODIUM; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; CATALYSIS; CHIRALITY; COMBINATORIAL CHEMISTRY; DRUG MIXTURE; ENANTIOMER; HYDROGENATION; LIGAND BINDING; METAL BINDING;

EID: 0037450022     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200390209     Document Type: Article

References (41)

1. a) W. S. Knowles, Angew. Chem. 2002, 114, 2096-2107; Angew. Chem. Int. Ed. 2002, 41, 199:3-2007;
2. a) W. S. Knowles, Angew. Chem. 2002, 114, 2096-2107; Angew. Chem. Int. Ed. 2002, 41, 199:3-2007;
3. b) R. Noyori, Angew. Chem. 2002, 114, 2108-2123; Angew. Chem. Int. Ed. 2002, 41, 2008-2022;
4. b) R. Noyori, Angew. Chem. 2002, 114, 2108-2123; Angew. Chem. Int. Ed. 2002, 41, 2008-2022;
5. c) K. B. Sharpless, Angew. Chem. 2002, 114, 2126-2135; Angew. Chem. Int. Ed. 2002, 41, 2024-2032.
6. c) K. B. Sharpless, Angew. Chem. 2002, 114, 2126-2135; Angew. Chem. Int. Ed. 2002, 41, 2024-2032.
7. Comprehensive Asymmetric Catalysis, Vol. I-III (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin, 1999.
8. See, for example: a) M. B. Francis, E. N. Jacobsen, Angew. Chem. 1999, 111, 987-991; Angew. Chem. Int. Ed. 1999, 38, 937-941;
9. See, for example: a) M. B. Francis, E. N. Jacobsen, Angew. Chem. 1999, 111, 987-991; Angew. Chem. Int. Ed. 1999, 38, 937-941;
10. b) S. R. Gilbertson, C.-W. T. Chang, Chem. Commun. 1997, 975-976;
11. c) C. Gennari, S. Ceccarelli, U. Piarulli, C. A. G. N. Montalbetti, R. F. W. Jackson, J. Org. Chem. 1998, 63, 5312-5313;
12. d) K. Burgess, H.-J. Lim, A. M. Porte, G. A. Sulikowski, Angew. Chem. 1996, 108, 192-194; Angew. Chem. Int. Ed. Engl. 1996, 35, 220-222;
13. d) K. Burgess, H.-J. Lim, A. M. Porte, G. A. Sulikowski, Angew. Chem. 1996, 108, 192-194; Angew. Chem. Int. Ed. Engl. 1996, 35, 220-222;
14. e) C.A. Krueger, K.W. Kuntz, C.D. Dzierba, W. G. Wirschun, J. D. Gleason, M. L. Snapper, A. H. Hoveyda, J. Am. Chem. Soc. 1999, 121, 4284-4285;
15. f) J. Long, J. Hu, X. Shen, B. Ji, K. Ding, J. Am. Chem. Soc. 2002, 124, 10-11;
16. g) A. Berkessel, R. Riedl, J. Comb. Chem. 2000, 2, 215-219;
17. h) S. Dahmen, S. Bräse, Synthesis 2001, 1431-1449.
18. Reviews of combinatorial and evolutionary methods for the generation of enantioselective (bio)catalysts as well as high-throughput screening systems: a) M. T. Reetz, Angew. Chem. 2001, 113, 292-320; Angew. Chem. Int. Ed. 2001, 40, 284-310;
19. Reviews of combinatorial and evolutionary methods for the generation of enantioselective (bio)catalysts as well as high-throughput screening systems: a) M. T. Reetz, Angew. Chem. 2001, 113, 292-320; Angew. Chem. Int. Ed. 2001, 40, 284-310;
20. b) M. T. Reetz, Angew. Chem. 2002, 114, 1391-1394; Angew. Chem. Int. Ed. 2002, 41, 1335-1338.
21. b) M. T. Reetz, Angew. Chem. 2002, 114, 1391-1394; Angew. Chem. Int. Ed. 2002, 41, 1335-1338.
22. Of course, transition-metal catalysts with two different types of ligands are known, for example, Noyori's Ru catalysts for asymmetric ketone reduction, composed of BINAP and a chiral diamine (whose proton is transferred onto the substrate).[1b] Both in the matched and mismatched case discrete diastereomeric catalyst systems having two different chelating ligands are involved. The corresponding BINAP-free and diamine-free Ru complexes are not catalytically active?[1b] In contrast, we employ two different mono-P ligands having the same absolute configuration with formation of three structurally different (not diastereomeric!) active catalysts which are in equilibrium with one another, the reactivity and selectivity of which differ.
23. I. V. Komarov, A. Börner, Angew. Chem. 2001, 113, 1237-1240; Angew. Chem. Int. Ed. 2001, 40, 1197-1200.
24. I. V. Komarov, A. Börner, Angew. Chem. 2001, 113, 1237-1240; Angew. Chem. Int. Ed. 2001, 40, 1197-1200.
25. a) M. T. Reetz, T. Sell, Tetrahedron Lett. 2000, 41, 6333-6336;
26. b) C. Claver, E. Fernandez, A. Gillon, K. Heslop, D. J. Hyett, A. Martorell, A. G. Orpen, P. G. Pringle, Chem. Commun. 2000, 961-962.
27. M. T. Reetz, G. Mehler, Angew. Chem. 2000, 112, 4047-4049; Angew. Chem. Int. Ed. 2000, 39, 3889-3890.
28. M. T. Reetz, G. Mehler, Angew. Chem. 2000, 112, 4047-4049; Angew. Chem. Int. Ed. 2000, 39, 3889-3890.
29. a) M. van den Berg, A. J. Minnaard, E. P. Schudde, J. van Esch, A. H. M. de Vries, J. G. de Vries, B. L. Feringa, J. Am. Chem. Soc. 2000, 122, 11539-11540;
30. b) A. J. Minnaard, M. van den Berg, E. P. Schudde, J. van Esch, A. H. M. de Vries, J. G. de Vries, B. L. Feringa, Chim. Oggi 2001, 19, 12-13.
31. Synthesis and hydrogenation of N-acyl enamines: a) M. J. Burk, G. Casy, N. B. Johnson, J. Org. Chem. 1998, 63, 6084-6085;
32. b) X. Jia, R. Guo, X. Li, X. Yao, A. S. C. Chan, Tetrahedron Lett. 2002, 43, 5541-5544;
33. c) A.-G. Hu, Y. Fu, J.-H. Xie, H. Zhou, L.-X. Wang, Q.-L. Zhou, Angew. Chem. 2002,114, 2454-2456; Angew. Chem. Int. Ed. 2002, 41, 2348-2350;
34. c) A.-G. Hu, Y. Fu, J.-H. Xie, H. Zhou, L.-X. Wang, Q.-L. Zhou, Angew. Chem. 2002,114, 2454-2456; Angew. Chem. Int. Ed. 2002, 41, 2348-2350;
35. d) W. Tang, X. Zhang, Angew. Chem. 2002, 114, 1682-1684; Angew. Chem. Int. Ed. 2002, 41, 1612-1614;
36. d) W. Tang, X. Zhang, Angew. Chem. 2002, 114, 1682-1684; Angew. Chem. Int. Ed. 2002, 41, 1612-1614;
37. e) S.-G. Lee, Y. J. Zhang, C. E. Song, J. K. Lee, J. H. Choi, Angew. Chem. 2002, 114, 875 -877; Angew. Chem. Int. Ed. 2002, 41, 847-849;
38. e) S.-G. Lee, Y. J. Zhang, C. E. Song, J. K. Lee, J. H. Choi, Angew. Chem. 2002, 114, 875 -877; Angew. Chem. Int. Ed. 2002, 41, 847-849;
39. f) M. T. Reetz, G. Mehler, A. Meiswinkel, T. Sell, Tetrahedron Lett. 2002, 43, 7941-7943.
40. M. T. Reetz, T. Sell, A. Meiswinkel, G. Mehler, patent application, DE-A 10247633.0 (11.10.2002).
41. In this heterocombination (60 % of total catalyst system) NMR spectroscopy shows the presence of two different species (R. Mynott, unpublished results). Detailed NMR studies are in progress.