Developments in asymmetric hydrogenation from an industrial perspective

Accounts of Chemical Research

Volumn 40, Issue 12, 2007, Pages 1385-1393

  Shimizu, Hideo ^a   Nagasaki, Izuru ^a   Matsumura, Kazuhiko ^a   Sayo, Noboru ^a   Saito, Takao ^a  

^a TAKASAGO INTERNATIONAL CORPORATION   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 38049004864     PISSN: 00014842     EISSN: None     Source Type: Journal    
DOI: 10.1021/ar700101x     Document Type: Review

References (82)

1. (a) Ohkuma, T.; Kitamura, M.; Noyori, R. Asymmetric Hydrogenation. In Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; Wiley-VCH: New York, 2000; pp 1-110.
2. (b) Tang, W.; Zhang, X. New Chiral Phosphorous Ligands for Enantioselective Hydrogenation. Chem. Rev. 2003, 103, 3029-3069.
3. (a) Kumobayashi, H. Industrial Application of Asymmetric Reactions Catalyzed by BINAP-Metal Complexes. Reel. Trav. Chim. Pays-Bas 1996, 115, 201-210.
4. (b) Kumobayashi, H.; Miura, T.; Sayo, N.; Saito, T.; Zhang, X. Recent Advances of BINAP Chemistry in the Industrial Aspects. Synlett 2001, 1055-1064.
5. (c) Blaser, H.-U.; Pugin, B.; Spindler, F. Enantioselective Synthesis. In Applied Homogeneous Catalysis with Organometallic Compounds, 2nd ed.; Cornils, B., Hermann, W. A., Eds.; Wiley-VCH: Weinheim, Germany, 2002; Vol. 3, pp 1131-1149.
6. (d) Blaser, H. U.; Malan, C.; Pugin, B.; Spindler, F.; Steiner, H.; Studer, M. Selective Hydrogenation for Fine Chemicals: Recent Trends and New Developments. Adv. Synth. Catal. 2003, 345, 103-151.
7. (e) Sumi, K.; Kumobayashi, H. Rhodium/Ruthenium Applications. Top. Organomet. Chem. 2004, 6, 63-95.
8. Miyashita, A.; Yasuda, A.; Takaya, H.; Toriumi, K.; Ito, T.; Souchi, T.; Noyori, R. Synthesis of 2,2′-Bis(diphenylphosphino)-1,1′-binaphthyl (BINAP), an Atropisomeric Chiral Bis(triaryl)phosphine, and Its Use in the Rhodium(I)-Catalyzed Asymmetric Hydrogenation of α-(Acylamino)acrylic Acids. J. Am. Chem. Soc. 1980, 102, 7932-7934.
9. (a) Ikariya, T.; Ishii, Y.; Kawano, H.; Arai, T.; Saburi, M.; Yoshikawa, S.; Akutagawa, S. Synthesis of Novel Chiral Ruthenium Complexes of 2,2′-Bis(diphenylphosphino)-1,1′-binaphthyl and Their Use as Asymmetric Catalysts. J. Chem. Soc., Chem. Commun. 1985, 922-924.
10. (b) Noyori, R.; Ohkuma, T.; Kitamura, M.; Takaya, H.; Sayo, N.; Kumobayashi, H.; Akutagawa, S. Asymmetric Hydrogenation of β-Ketoesters. A Practical, Purely Chemical Access to β-Hydroxy Esters in High Enantiometric Purity. J. Am. Chem. Soc. 1987, 109, 5856-5858.
11. (c) Ohkuma, T.; Ooka, H.; Hashiguchi, S.; Ikariya, T.; Noyori, R. Practical Enantioselective Hydrogenation of Aromatic Ketones. J. Am. Chem. Soc. 1995, 117, 2675-2676.
12. (a) Akutagawa, S. A. Practical Synthesis of (-)-Menthol with the Rh-BINAP Catalyst. In Chirality in Industry: The Commercial Manufacture and Applications of Optically Active Compounds; Collins, A. N., Sheldrake, G. N., Crosby, J., Eds.; Wiley: Chichester, 1995; pp 313-324.
13. (b) Otsuka, S. Discoveries of the Catalysis of Asymmetric Isomerization of Allylamines and Its Significance in Science and Industry. Acta Chem. Scand. 1996, 50, 353-360.
14. Shimizu, H.; Nagasaki, I.; Saito, T. Recent Advances in Biaryl-Type Bisphosphine Ligands. Tetrahedron 2005, 61, 5405-5432.
15. (a) Mashima, K.; Matsumura, Y.-I.; Kusano, K.-H.; Kumobayashi, H.; Sayo, N.; Hori, Y.; Ishizaki, T.; Akutagawa, S.; Takaya, H. Highly Stereoselective Asymmetric Hydrogenation of 2-Benzamidomethyl-3-oxobutanoate Catalysed by Cationic Binap-Ruthenium(II) Complexes. J. Chem. Soc., Chem. Commun. 1991, 609-610.
16. (b) Mashima, K.; Kusano, K.-H.; Sato, N.; Matsumura, Y.-I.; Nozaki, K.; Kumobayashi, H.; Sayo, N.; Hori, Y.; Ishizaki, T.; Akutagawa, S.; Takaya, H. Cationic BINAP-Ru(II) Halide Complexes: Highly Efficient Catalysts for Stereoselective Asymmetric Hydrogenation of α- and β-Functionalized Ketones. J. Org. Chem. 1994, 59, 3064-3076.
17. Takaya, H.; Mashima, K.; Koyano, K.; Yagi, M.; Kumobayashi, H.; Taketomi, T.; Akutagawa, S.; Noyori, R. Practical Synthesis of (R)-or (S)-2,2′-Bis(diarylphosphino)-1,1′-binaphthyls (BINAPs). J. Org. Chem. 1986, 51, 629-635.
18. (a) Cai, D.; Payack, J. F.; Bender, D. R.; Hughes, D. L.; Verhoeven, T. R.; Reider, P. J. Synthesis of Chiral 2,2′-Bis(diphenylphosphino)-1, 1′-binaphthyl (BINAP) via a Novel Nickel-Catalyzed Phosphine Insertion. J. Org. Chem. 1994, 59, 7180-7181.
19. (b) Cai, D.; Payack, J. F.; Bender, D. R.; Hughes, D. L.; Verhoeven, T. R.; Reider, P. J. (R)-(+)- and (S)-(-)-2,2′-Bis(diphenylphosphino)-1, 1′-binaphthyl (BINAP). Org. Synth. 1999, 76, 6-11.
20. (a) Sayo, N.; Zhang, X.; Ohmoto, T.; Yoshida, A.; Yokozawa, T. Method for Producing an Optically Active Diphosphine. Eur. Patent 0,771,812, 1997.
21. (b) Zhang, X.; Sayo, N. Method of Preparing Optically Active Diphosphine Ligands. Eur. Patent 0,839,819, 1998.
22. Ager, D. J.; Laneman, S. A. Convenient and Direct Preparation of Tertiary Phosphines via Nickel-Catalysed Cross-coupling. Chem. Commun. 1997, 2359-2360.
23. Inoue, S.-I.; Osada, M.; Koyano, K.; Takaya, H.; Noyori, R. Asymmetric Hydrogenation of Geraniol and Nerol Catalyzed by BINAP-Rhodium(I) Complexes. Chem. Lett. 1985, 1007-1008.
24. Schmid, R.; Cereghetti, M.; Heiser, B.; Schonholzer, P.; Hansen, H.J. Axially Dissymmetric Bis(triaryl)phosphines in the Biphenyl Series: Synthesis of (6,6′-Dimethylbiphenyl-2,2′-diyl)bis(diphenylphosphine) ('BIPHEMP') and Analogues, and Their Use in Rh(I)-Catalyzed Asymmetric Isomerizations of N,N-Diethylnerylamine. Helv. Chim. Acta 1988, 71, 897-929.
25. Schmid, R.; Foricher, J.; Cereghetti, M.; Schönholzer, P. Axially Dissymmetric Diphosphines in the Biphenyl Series: Synthesis of (6,6′-Dimethoxylbiphenyl-2,2′-diyl)bis(diphenylphosphine) ('MeO-BIPHEP') and Analogues via an ortho-Lithiation/Iodination Ullmann-Reaction Approach. Helv. Chim. Acta 1991, 74, 370-388.
26. 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.
27. Shimizu, H.; Ishizaki, T.; Fujiwara, T.; Saito, T. A Novel Approach for Investigating Enantioselectivity in Asymmetric Hydrogenation. Tetrahedron: Asymmetry 2004, 15, 2169-2172.
28. Shimizu, H.; Saito, T.; Nagasaki, I. Phosphine Compounds, Transition Metal Complexes with the Compounds Contained as Ligands Therein, and Asymmetric Synthesis Catalysts Containing the Complexes. U.S. Patent 7,078,568 B2, 2006.
29. Shimizu, H.; Nagasaki, I.; Sayo, N.; Saito, T. In Trivalent Phosphorous Ligands for Asymmetric Synthesis; Börner, A., Ed.; Wiley-VCH: Weinheim,to be published.
30. Lipshutz, B. H.; Servesko, J. M.; Petersen, T. B.; Papa, P. P.; Lover, A. A. Asymmetric 1,4-Reductions of Hindered β-Substituted Cycloalkenones Using Catalytic SEGPHOS-Ligated CuH. Org. Lett. 2004, 6, 1273-1275.
31. (a) Hoekstra, W. J. The Chemistry and Biology of β-Amino Acids. Curr. Med. Chem. 1999, 6, 905-1004.
32. (b) Enantioselective Synthesis of β-Amino Acids, 2nd ed.; Juaristi, E., Soloshonok, V. A., Eds.; Wiley & Sons: New York, 2004.
33. (a) Lubell, W. D.; Kitamura, M.; Noyori, R. Enantioselective Synthesis of β-Amino Acids Based on BINAP-ruthenium(II) Catalyzed Hydrogenation. Tetrahedron: Asymmetry 1991, 2, 543-554.
34. (b) Zhu, G.; Chen, Z.; Zhang, X. Highly Efficient Asymmetric Synthesis of β-Amino Acid Derivatives via Rhodium-Catalyzed Hydrogenation of β-(Acylamino)acrylates. J. Org. Chem. 1999, 64, 6907-6910.
35. (c) Heller, D.; Holz, J.; Drexler, H.-J.; Lang, J.; Drauz, K.; Krimmer, H.-P.; Borner, A. Pressure Dependent Highly Enantioselective Hydrogenation of Unsaturated β-Amino Acid Precursors. J. Org. Chem. 2001, 66, 6816-6817.
36. (d) Drexler, H.-J.; You, J.; Zhang, S.; Fischer, C.; Baumann, W.; Spannenberg, A.; Heller, D. Chiral β-Amino Acid Derivatives via Asymmetric Hydrogenation. Org. Proc. Res. Dev. 2003, 7, 355-361.
37. (a) Matsumura, K.; Zhang, X.; Saito, T. Method for Producing an Optically Active Beta-Amino Acid. U.S. Patent 7,015,348 B2, 2004.
38. (b) Matsumura, K.; Hori, K.; Kakizawa, T.; Saito, T. Catalytic Asymmetric Synthesis of β-Amino Acid Derivatives. In Proceedings of the Summer Symposium, Tokyo, July 28-29, 2005, The Japanese Society for Process Chemistry: Tokyo; pp 146-147.
39. (c) Saito, T.; Zhang, X.; Matsumura, K.; Yokozawa, T.; Shimizu, H. Development Strategy of SEGPHOS and Smart Approaches to β-Amino Acids. In 19th North American Meeting, Philadelphia, PA, May 22-27, 2005, North American Catalysis Society Home Page. http://www.nacatsoc.org/19nam/abstracts/O_224.pdf.
40. Hsiao, Y.; Rivera, N. R.; Rosner, T.; Krska, S. W.; Njolito, E.; Wang, F.; Sun, Y.; Armstrong, J. D.; Grabowski, E. J. J.; Tillyer, R. D.; Spindler, F.; Malan, C. Highly Efficient Synthesis of β-Amino Acid Derivatives via Asymmetric Hydrogenation of Unprotected Enamines. J. Am. Chem. Soc. 2004, 126, 9918-9919.
41. (a) Matsumura, K.; Saito, T. Asymmetric Reductive Amination of Keto Acid Derivatives for Producing Amino Acid Derivatives. PCT Patent Appl. WO2005,028,419 A3, 2005.
42. The Lanxess group reported a similar reaction system using a Ru-CIMeO-BIPHEP catalyst: (b) Bunlaksananusorn, T.; Rampf, F. A Facile One-pot Synthesis of Chiral β-Amino Esters. Synlett 2005, 2682-2684.
43. Noyori, R.; Ohta, M.; Hsiao, Y.; Kitamura, M.; Ohta, T.; Takaya, H. Asymmetric Synthesis of Isoquinoline Alkaloids by Homogeneous Catalysis. J. Am. Chem. Soc. 1986, 108, 7117-7119.
44. Creamer, M. Ruthenium Price Soars to Great Heights. Mining Weekly Online Home Page. http://www.miningweekly.co.za (accessed April 2007).
45. (a) Bartók, M. Carbonyl Compounds. In Stereochemistry of Heterogeneous Metal Catalysis; Wiley & Sons: Chichester, UK, 1985; pp 335-382.
46. (b) Nishimura, S. Copper Catalysts. In Handbook of Heterogeneous Catalytic Hydrogenation for Organic Synthesis; Wiley & Sons: New York, 2001; pp 26-28.
47. 2. J. Am. Chem. Soc. 1989, 111, 8818-8823.
48. (b) Stryker, J. M.; Mahoney, W. S.; Daeuble, J. F.; Brestensky, D. M. Hydride-Mediated Homogeneous Catalysis: Chemoselective Catalytic Hydride Reductions via Heterolytic Hydrogen Activation. In Catalysis of Organic Reactions; Pascoe, W. E., Ed.; Marcel Dekker: New York, 1992; pp 29-44.
49. 2. In Catalysis of Organic Reactions; Sacros, M. G., Prunier, M. L., Eds.; Marcel Dekker: New York, 1995; pp 235-247.
50. (d) Chen, J.-X.; Daeuble, J. F.; Brestensky, D. M.; Stryker, J. M. Highly Chemoselective Catalytic Hydrogenation of Unsaturated Ketones and Aldehydes to Unsaturated Alcohols Using Phosphine-Stabilized Copper(I) Hydride Complexes. Tetrahedron 2000, 56, 2153-2166.
51. (e) Chen, J.-X.; Daeuble, J. F.; Stryker, J. M. Phosphine Effects in the Copper(I) Hydride-Catalyzed Hydrogenation of Ketones and Regioselective 1,2-Reduction of α,β- Unsaturated Ketones and Aldehydes. Hydrogenation of Decalin and Steroidal Ketones and Enones. Tetrahedron 2000, 56, 2789-2798.
52. For reviews: (a) Riant, O.; Mostefai, N.; Coumarcel, J. Recent Advances in the Asymmetric Hydrosilylation of Ketones, Imines and Electrophilic Double Bonds. Synthesis 2004, 2943-2958.
53. (b) Rendler, S.; Oestreich, M. Polishing a Diamond in the Rough: "Cu-H" Catalysis with Silanes. Angew. Chem., Int. Ed. 2007, 46, 498-504.
54. Lipshutz, B. H.; Papa, P. Copper-Catalyzed Reductive Alkylations of Enones: A Novel Transmetalation Protocol. Angew. Chem., Int. Ed. 2002, 41, 4580-4582.
55. Yang, J. W.; List, B. Catalytic Asymmetric Transfer Hydrogenation of α-Ketoesters with Hantzsch Esters. Org. Lett. 2006, 8, 5653-5655.
56. Heterogeneous Cu-catalyzed asymmetric hydrogenation was reported but with limited enantioselectivity: Klabunovskii, E. I.; Vedenyapin, A. A.; Airapetov, Y. S.; Fridman, Y. D. Enantioselective Hydrogenation on Heterogeneous Metal Catalysts. React. Kinet. Catal. Lett. 1978, 9, 73-77.
57. 2. Inorg. Chem. 1972, 11, 1818-1825.
58. (b) Bezman, S. A.; Churchill, M. R.; Osborn, J. A.; Wormald, J. Preparation and Crystallographic Characterization of a Hexameric Triphenylphosphinecopper Hydride Cluster. J. Am. Chem. Soc. 1971, 93, 2063-2065.
59. (a) Appella, D. H.; Moritani, Y.; Shintani, R.; Ferreira, E. M.; Buchwald, S. L. Asymmetric Conjugate Reduction of α,β-Unsaturated Esters Using a Chiral Phosphine-Copper Catalyst. J. Am. Chem. Soc. 1999, 121, 9473-9474.
60. (b) Moritani, Y.; Appella, D. H.; Jurkauskas, V.; Buchwald, S. L. Synthesis of β-Alkyl Cyclopentanones in High Enantiomeric Excess via Copper-Catalyzed Asymmetric Conjugate Reduction. J. Am. Chem. Soc. 2000, 122, 6797-6798.
61. (c) Hughes, G.; Kimura, M.; Buchwald, S. L. Catalytic Enantioselective Conjugate Reduction of Lactones and Lactams. J. Am. Chem. Soc. 2003, 125, 11253-11258.
62. (a) Lipshutz, B. H.; Noson, K.; Chrisman, W. Ligand-Accelerated, Copper-Catalyzed Asymmetric Hydrosilylations of Aryl Ketones. J. Am. Chem. Soc. 2001, 123, 12917-12918.
63. (b) Sirol, S.; Courmarcel, J.; Mostefai, N.; Riant, O. Efficient Enantioselective Hydrosilylation of Ketones Catalyzed by Air Stable Copper Fluoride-Phosphine Complexes. Org. Lett. 2001, 3, 4111-4113.
64. (c) Lipshutz, B. H.; Lower, A.; Noson, K. Copper(I) Hydride-Catalyzed Asymmetric Hydrosilylation of Heteroaromatic Ketones. Org. Lett. 2002, 4, 4045-4048.
65. (d) Lipshutz, B. H.; Noson, K.; Chrisman, W.; Lower, A. Asymmetric Hydrosilylation of Aryl Ketones Catalyzed by Copper Hydride Complexed by Nonracemic Biphenyl Bis-phosphine Ligands. J. Am. Chem. Soc. 2003, 125, 8779-8789.
66. (e) Lipshutz, B. H.; Lower, A.; Kucejko, R. J.; Noson, K. Applications of Asymmetric Hydrosilylations Mediated by Catalytic (DTBM-SEGPHOS)CuH. Org. Lett. 2006, 8, 2969-2972.
67. Lipshutz, B. H.; Shimizu, H. Copper(I)-Catalyzed Asymmetric Hydrosilylations of Imines at Ambient Temperatures. Angew. Chem., Int. Ed. 2004, 43, 2228-2230.
68. (a) Czekelius, C.; Carreira, E. M. Catalytic Enantioselective Conjugate Reduction of β,β-Disubstituted Nitroalkenes. Angew. Chem., Int. Ed. 2003, 42, 4793-4795.
69. (b) 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.
70. 2. Org. Lett. 2004, 6, 4575-4577.
71. (d) Ren, Y.; Xu, X.; Sun, K.; Xu, J. Tetrahedron: Asymmetry 2005, 16, 4010-4014.
72. Bakos, J.; Tóth, I.; Markó, L. Use of Heterogeneous Asymmetric Hydrogenation for the Preparation of a Chiral Phosphinite and Its Application as a Ligand in Homogeneous Asymmetric Hydrogenation. J. Org. Chem. 1981, 46, 5427-5428.
73. Gysling, H. J. Coordination Complexes of Copper(I) Nitrate. Inorg. Synth. 1979, 19, 92-96.
74. Shimizu, H.; Igarashi, D.; Kuriyama, W.; Yusa, Y.; Sayo, N.; Saito, T. Asymmetric Hydrogenation of Aryl Ketones Mediated by a Copper Catalyst. Org. Lett. 2007, 9, 1655-1657.
75. Fryzuk, M. D.; Bosnich, B. Asymmetric Synthesis. Production of Optically Active Amino Acids by Catalytic Hydrogenation. J. Am. Chem. Soc. 1977, 99, 6262-6267.
76. Dang, T. P.; Kagan, H. B. The Asymmetric Synthesis of Hydratropic Acid and Amino-acids by Homogeneous Catalytic Hydrogenation. Chem. Commun. 1971, 481.
77. Achiwa, K. Asymmetric Hydrogenation with New Chiral Functionalized Bisphosphine-Rhodium Complexes. J. Am. Chem. Soc. 1976, 98, 8265-8266.
78. Togni, A.; Breutel, C.; Schnyder, A.; Spindler, F.; Landert, H.; Tijani, A. A Novel Easily Accessible Chiral Ferrocenyldiphosphine for Highly Enantioselective Hydrogenation, Allylic Alkylation, and Hydroboration Reactions. J. Am. Chem. Soc. 1994, 116, 4062-4066.
79. Noyori, R.; Ohkuma, T. Asymmetric Catalysis by Architectural and Functional Molecular Engineering: Practical Chemo- and Stereoselective Hydrogenation of Ketones. Angew. Chem., Int. Ed. 2001, 40, 40-73.
80. (a) Sheldon, R. A. Chirotechnology: the Industrial Synthesis of Optically Active Compounds; Marcel Dekker: New York, 1993.
81. (b) Sheldon, R. A.; Arends, I.; Hanefeld, U. Green Chemistry and Catalysis; Wiley-VCH: Weinheim, 2007.
82. Based on this philosophy, Takasago's chiral ligands and Ru catalysts became commercially available.