From a chiral switch to a ligand portfolio for asymmetric catalysis

Accounts of Chemical Research

Volumn 40, Issue 12, 2007, Pages 1240-1250

  Blaser, Hans Ulrich ^a   Pugin, Benoît ^a   Spindler, Felix ^a   Thommen, Marc ^a,b  

^a SOLVIAS AG   (Switzerland)

^b DSM NUTRITIONAL PRODUCTS LTD   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

ACETAMIDE DERIVATIVE; LIGAND; METOLACHLOR; PHOSPHINE DERIVATIVE; PHOSPHORUS;

CATALYSIS; CHEMISTRY; REVIEW; STEREOISOMERISM;

ACETAMIDES; CATALYSIS; LIGANDS; PHOSPHINES; PHOSPHORUS; STEREOISOMERISM;

EID: 38049036296     PISSN: 00014842     EISSN: None     Source Type: Journal    
DOI: 10.1021/ar7001057     Document Type: Review

References (47)

1. Ramos Tombo, G. M.; Blaser, H. U. Chirality in agrochemistry: An established technology and its impact on the development of industrial stereoselective catalysis. In Pesticide Chemistry and Bioscience; Brooks, G. T., Roberts, T. R., Eds.; Royal Society of Chemistry: Cambridge, U.K., 1999; pp 33-54, and references therein.
2. Moser, H.; Rihs, G.; Sauter, H. P. Effect of atropisomerism and chiral center on the biological activity of Metolachlor. Z. Naturforsch., B: Chem. Sci. 1982, 37, 451-462.
3. Spindler, F.; Pugin, B.; Jalett, H. P.; Buser, H. P.; Pittelkow, U.; Blaser, H. U. A technically useful catalyst for the homogeneous hydrogenation of N-aryl imines: A case study. Chem. Ind. 1996, 68, 153-166.
4. Blaser, H. U.; Buser, H. P.; Coers, K.; Hanreich, R.; Jalett, H. P.; Jelsch, E.; Pugin, B.; Schneider, H. D.; Spindler, F.; Wegmann, A. The chiral switch of metolachlor: The development of a large scale enantioselective catalytic process. Chimia 1999, 53, 275-280.
5. Blaser, H. U. The chiral switch of (S)-metolachlor: A personal account of an industrial odyssey in asymmetric catalysis. Adv. Synth. Catal. 2002, 344, 17-31.
6. Vineyard, B. D.; Knowles, W. S.; Sabacky, M. J.; Bachman, G. L.; Weinkauff, D. J. Asymmetric hydrogenation. Rhodium chiral bisphosphine catalyst. J. Am. Chem. Soc. 1977, 99, 5946-5952.
7. Orito, Y.; Imai, S.; Niwa, S. Asymmetric hydrogenation of methyl pyruvate using the Pt-C catalyst modified with cinchonidine. J. Chem. Soc. Jpn. 1979, 1118-1120.
8. Cullen, W. R.; Fryzuk, M. D.; James, B. R.; Kutney, J. P.; Kang, G.-J.; Herb, G.; Thorburn, I. S.; Spogliarich, R. Asymmetric homogeneous hydrogenation of imines using rhodium-phosphine systems. J. Mol. Catal. 1990, 62, 243-253.
9. Crabtree, R. H.; Felkin, H.; Fillebeen-Khan, T.; Morris, G. E. Dihydridoiridium diolefin complexes as intermediates in homogeneous hydrogenation. J. Organometal. Chem. 1979, 168, 183-195.
10. Spindler, F.; Pugin, B.; Blaser, H. U. New iridium diphosphin complexes for the enantioselective hydrogenation of imines. Angew. Chem., Int. Ed. 1990, 29, 558-559.
11. Togni, A. Developing new chiral ferrocenyl ligands for asymmetric catalysis. A personal account. Chimia 1996, 50, 86-93.
12. Hofer, R. In Kaisten, Syngenta operates the world's largest plant in which an enantioselective catalytic hydrogenation is performed. How did this come about. Chimia 2004, 59, 10-12.
13. Bader, R.; Baumeister, P.; Blaser, H. U. Catalysis at Ciba-Geigy. Chimia 1996, 50, 99-105.
14. Blaser, H. U.; Brieden, W.; Pugin, B.; Spindler, F.; Studer, M.; Togni, A. Solvias Josiphos ligands: From discovery to technical application. Top. Catal. 2002, 19, 3-16.
15. Blaser, H. U.; Plogmann, D.; Studer, M. A direct way for solving synthetic and analytical problems. Chimia 2000, 54, 219-227.
16. For more details, see Blaser, H. U.; Spindler, F.; Thommen, M. Industrial applications. In Handbook of Homogeneous Hydrogenation; de Vries, J. G., Elsevier, C. J., Eds.; Wiley-VCH: Weinheim, Germany, 2007; pp 1279-1324.
17. Spindler, F.; Blaser, H. U. The highly enantioselective hydrogenation of N-phosphinylketimines with cationic Rh ferrocenyldiphosphine catalysts. Adv. Synth. Catal. 2001, 343, 68-70.
18. Czekelius, C.; Carreira, E. M. Catalytic enantioselective conjugate reduction of β,β-disubstituted nitroalkenes. Angew. Chem., Int. Ed. 2003, 42, 4793-4795.
19. Lipshutz, B. H.; Servesko, J. M. CuH-catalyzed asymmetric conjugate reductions of acyclic enones. Angew. Chem., Int. Ed. 2003, 42, 4789-4792.
20. Lipshutz, B. H.; Servesko, J. M.; Taft, B. R. Asymmetric 1,4-hydrosilylations of α,β-unsaturated esters. J. Am. Chem. Soc. 2004, 126, 8352-8353.
21. Lee, D.; Kim, D.; Yun, J. Highly enantioselective conjugate reduction of β,β-disubstituted α,β-unsaturated nitriles. Angew. Chem., Int. Ed. 2006, 45, 2785-2787.
22. Lopez, F.; Harutyunyan, S. R.; Meetsma, A.; Minnaard, A. J.; Feringa, B. L. Copper-catalyzed enantioselective conjugate addition of Grignard reagents to α,β-unsaturated esters. Angew. Chem., Int. Ed. 2005, 44, 2752-2756.
23. Lautens, M.; Fagnou, K.; Hiebert, S. Transition metal-catalyzed enantioselective ring-opening reactions of oxabicyclic alkenes. Acc. Chem. Res. 2003, 36, 48-58.
24. Bercot, E. A.; Rovis, T. A. Palladium-catalyzed enantioselective alkylative desymmetrization of meso-succinic anhydrides. J. Am. Chem. Soc. 2004, 126, 10248-10249.
25. Sturm, T.; Xiao, L.; Weissensteiner, W. Preparation of novel enantiopure ferrocenyl-based ligands for asymmetric catalysis. Chimia 2001, 55, 688-693.
26. Sturm, T.; Weissensteiner, W.; Spindler, F. A novel class of ferrocenyl-aryl-based diphosphine ligands for Rh- and Ru-catalysed enantioselective hydrogenation. Adv. Synth. Catal. 2003, 345, 160-164.
27. Houpis, I. N.; Patterson, L. E.; Alt, C. A.; Rizzo, J. R.; Zhang, T. Y.; Haurez, M. Synthesis of PPAR agonist via asymmetric hydrogenation of a cinnamic acid derivative and stereospecific displacement of (S)-2-chloropropionic acid. Org. Lett. 2005, 7, 1947-1950.
28. Tanaka, K.; Hagiwara, Y.; Noguchi, K. Rhodium-catalyzed regio-and enantioselective intermolecular [4 + 2] carbocyclization of 4-alkynals with N,N-dialkylacrylamides. Angew. Chem., Int. Ed. 2005, 44, 7260-7263.
29. Kong, J.-R.; Ngai, M.-Y.; Krische, M. J. Highly enantioselective direct reductive coupling of conjugated alkynes and α-ketoesters via rhodium-catalyzed asymmetric hydrogenation. J. Am. Chem. Soc. 2006, 128, 718-719.
30. Blaser, H. U.; Lotz, M.; Spindler, F. Asymmetric hydrogenation of alkenes with ferrocene based ligands. In Handbook of Homogeneous Hydrogenation; de Vries, J. G., Elsevier, C. J., Eds.; Wiley-VCH: Weinheim, Germany, 2007; pp 833-851.
31. Ireland, T.; Grossheimann, G.; Wieser-Jeunesse, C.; Knochel, P. Ferrocenyl ligands with two phosphanyl substituents in the appositions for the transition metal catalyzed asymmetric hydrogenation of functionalized double bonds. Angew. Chem., Int. Ed. 1999, 38, 3212-3215.
32. 2-symmetrical ferrocenyl ligands: highly enantioselective Rh-catalyzed hydrogenation of α-acetamidoacrylic acid derivatives. Tetrahedron Lett. 1998, 39, 8073-8076.
33. Spindler, F.; Malan, C.; Lotz, M.; Kesselgruber, M.; Pittelkow, U.; Rivas-Nass, A.; Briel, O.; Blaser, H. U. Modular chiral ligands: The profiling of Mandyphos and Taniaphos. Tetrahedron: Asymmetry 2004, 15, 2299-2306.
34. Hashmi, A. S. K.; Haufe, P.; Schmid, C.; Rivas Nass, A.; Frey, W. Asymmetric rhodium-catalyzed hydrogenation meets gold-catalyzed cyclization: Enantioselective synthesis of 8-hydroxytetrahydroisoquinolines. Chem. - Eur. J. 2006, 12, 5376-5382.
35. Lautens, M.; Fagnou, K.; Zunic, V. An expedient enantioselective route to diaminotetralins: Application in the preparation of analgesic compounds. Org. Lett. 2002, 4, 3465-3468.
36. Llamas, T.; Gomez Arrayas, R.; Carretero, J. C. Catalytic enantioselective 1,3-dipolar cycloaddition of azomethine ylides with vinyl sulfones. Org. Lett. 2006, 8, 1795-1798.
37. Cobley, C. J.; Moran, P. H. Enantioselective hydrogenation: Phospholane ligands. In Handbook of Homogeneous Hydrogenation; de Vries, J. G., Elsevier, C. J., Eds.; Wiley-VCH: Weinheim, Germany, 2007; pp 773-831.
38. Ohkuma, T.; Noyori R. Asymmetric enantioselective ketone and β-keto ester hydrogenation (including mechanisms). In Handbook of Homogeneous Hydrogenation; de Vries, J. G., Elsevier, C. J., Eds.; Wiley-VCH: Weinheim, Germany, 2007; pp 1105-1163.
39. Burk, M. J. Modular phospholane ligands in asymmetric catalysis. Acc. Chem. Res. 2000, 33, 363-372.
40. Holz, J.; Quirmbach, M.; Schmidt, U.; Heller, D.; Stuermer, R.; Boerner, A. Synthesis of a new class of functionalized chiral bisphospholane ligands and the application in enantioselective hydrogenations. J. Org. Chem. 1998, 63, 8031-8034.
41. Kesselgruber, M.; Thommen, M. Phospholane salts and their use in enantioselective hydrogenation. EP 1622918, 2003 (CAN 141: 428385), assigned to Solvias AG.
42. Berens, U.; Englert, U.; Geyser, S.; Runsink, J.; Salzer, A. A flexible approach to different bidentate PP ligands as highly efficient ligands for asymmetric catalysis. Eur. J. Org. Chem. 2006, 2100-2109.
43. Schmid, R.; Broger, E. A.; Cereghetti, M.; Crameri, Y.; Foricher, J.; Lalonde, M.; Muller, R. K.; Scalone, M.; Schoettel, G.; Zutter, U. New developments in enantioselective hydrogenation. Pure Appl. Chem. 1996, 68, 131-138.
44. Saito, T.; Yokozawa, T.; Ishizaki, T.; Moroi, T.; Sayo, N.; Miura, T.; Kumobayashi, H. New chiral diphosphine ligands designed to have a narrow dihedral angle in the biaryl backbone. Adv. Synth. Catal. 2001, 343, 264-267.
45. Pugin, B.; Martin, P.; Müller, M.; Naud, F.; Spindler, F.; Thommen, M.; Melone, G., Kesselgruber, M. Amine-substituted diphenyldiphosphines and its application in asymmetric synthetic metal complexes for asymmetric addition reactions. EP 1611114, 2003, assigned to Solvias AG.
46. Pfaltz, A.; Blankenstein, J.; Hilgraf, R.; Hoermann, E.; McIntyre, S.; Menges, F.; Schoenleber, M.; Smidt, S. P.; Wuestenberg, B.; Zimmermann, N. Iridium-catalyzed enantioselective hydrogenation of olefins. Adv. Synth. Catal. 2003, 345, 33-43.
47. Naud, F.; Malan, C.; Spindler, F.; Rüggeberg, C.; Schmidt, A. T.; Blaser, H. U. Ru-(phosphino-oxazoline) complexes as effective, industrially viable catalysts for the enantioselective hydrogenation of aryl ketones. Adv. Synth. Catal. 2006, 348, 47-50.