Development of practical rhodium phosphine catalysts for the hydrogenation of β-dehydroamino acid derivatives

Organic Process Research and Development

Volumn 11, Issue 3, 2007, Pages 568-577

  Enthaler, Stephan ^a   Erre, Giulia ^a   Junge, Kathrin ^a   Holz, Jens ^a   Börner, Armin ^a   Alberico, Elisabetta ^b   Nieddu, Ilenia ^c   Gladiali, Serafino ^c   Beller, Matthias ^a  

^a UNIVERSITY OF ROSTOCK   (Germany)

^b CNR Consiglio Nazionale delle Ricerche   (Italy)

^c UNIVERSITY OF SASSARI   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 34748816570     PISSN: 10836160     EISSN: None     Source Type: Journal    
DOI: 10.1021/op0602270     Document Type: Article

References (103)

1. (a) Guénard, D.; Guritte-Voegelein, R.; Potier, P. Acc. Chem. Res. 1993, 26, 160-167.
2. (b) Cole, D. C. Tetrahedron 1994, 50, 9517-9582.
3. (c) Juaristi, E.; Soloshonok, V. Enantioselective Synthesis of β-amino acids, 2nd ed.; Wiley-Interscience: New Jersey, 2005.
4. (d) Lui, M.; Sibi, M. P. Tetrahedron 2002, 58, 7991-8035.
5. (e) Drexler, H.-J.; You, J.; Zhang, S.; Fischer, C.; Baumann, W.; Spannenberg, A.; Heller, D. Org. Process Res. Dev. 2003, 7, 355-361.
6. (f) Ma, J. Angew. Chem. 2003, 115, 4426-4435.
7. (g) Cheng, R. P.; Gellman, S. H.; DeGrado, W. F. Chem. Rev. 2001, 101, 3219-3232.
8. (h) Kubota, D.; Ishikawa, M.; Yamamoto, M.; Murakami, S.; Hachisu, M.; Katano, K.; Ajito, K., Bioorg. Med. Chem. 2006, 7, 2089-2108.
9. (a) Gellman, S. H., Acc. Chem. Res. 1998, 31, 173-180.
10. (b) Seebach, D.; Matthews, J. L. Chem. Commun. 1997, 2015-2022.
11. (a) Vineyard, B. D.; Knowles, W. S.; Sabacky, M. J.; Bachman, G. L.; Weinkauff, D. J. J. Am. Chem. Soc. 1977, 99, 5947-5952.
12. (b) Achiwa, K.; Soga, T. Tetrahedron Lett. 1978, 13, 1119-1120.
13. (c) Lubell, W. D.; Kitamura, M.; Noyori, R. Tetrahedron: Asymmetry 1991, 2, 543-554.
14. (d) Zhu, G.; Chen, Z.; Zhang, X. J. Org. Chem. 1999, 64, 6907-6910.
15. (e) Heller, D.; Holz, J.; Drexler, H.-J.; Lang, J.; Drauz, K.; Krimmer, H.-P.; Börner, A. J. Org. Chem. 2001, 66, 6816-6817.
16. (f) Yasutake, M.; Gridnev, I. D.; Higashi, N.; Imamoto, T. Org. Lett. 2001, 3, 1701-1704.
17. (g) Heller, D.; Drexler, H.-J.; You, J.; Baumann, W.; Drauz, K.; Krimmer, H.-P.; Börner, A. Chem. Eur. J. 2002, 8, 5196-5203.
18. (h) Zhou, Y.-G.; Tang, W.; Wang, W.-B.; Li, W.; Zhang, X. J. Am. Chem. Soc. 2002, 124, 4952-4953.
19. (i) Yang, W.; Wu, S.; Zhang, X. J. Am. Chem. Soc. 2003, 125, 9570-9571.
20. (j) Komarov, I. V.; Monsees, A.; Spannenberg, A.; Baumann, W.; Schmidt, U.; Fischer, C.; Börner, A. Eur. J. Org. Chem. 2003, 138-150.
21. (k) You, J.; Drexler, H.-J.; Zhang, S.; Fischer, C.; Heller, D. Angew. Chem. 2003, 115, 942-945.
22. (l) Holz, J.; Monsees, A.; Jiao, H.; You, J.; Komarov, I. V.; Fischer, C.; Drauz, K.; Börner, A. J. Org. Chem. 2003, 68, 1701-1707.
23. (m) Wu, J.; Chen, X.; Guo, R.; Yeung, C.-h.; Chan, A. S. C. J. Org. Chem. 2003, 68, 2490-2493.
24. (n) Henschke, J. P.; Burk, M. J.; Malan, C. G.; Herzberg, D.; Peterson, J. A.; Wildsmith, A. J.; Cobley, C. J.; Casy, G. Adv. Synth. Catal. 2003, 345, 300-307.
25. (o) Robinson, A. J.; Lim, C. Y.; He, L.; Ma, P.; Li, H.-Y. J. Org. Chem. 2001, 66, 4141-4147.
26. (p) Robinson, A. J.; Stanislawski, P.; Mulholland, D.; He, L.; Li, H.-Y. J. Org. Chem. 2001, 66, 4148-4152.
27. (q) Wu, H.-P.; Hoge, G. Org. Lett. 2004, 6, 3645-3647.
28. (r) Hsiao, Y.; Rivera, N. R.; Rosner, T.; Krska, S. W.; Njolito, E.; Wang, F.; Sun, Y.; Armstrong, J. D., III; Grabowski, E. J. J.; Tillyer, R. D.; Spindler, F.; Malan, C. J. Am. Chem. Soc. 2004, 126, 9918-9919.
29. (s) Dai. Q.; Yang, W.; Zhang, X. Org. Lett. 2005, 7, 5343-5345.
30. (t) Hansen, K. B.; Rosner, T.; Kubryk, M.; Dormer, P. G.; Armstrong, J. D., III. Org. Lett. 2005, 7, 4935-4938.
31. (u) Drexler, H.-J.; Baumann, W.; Schmidt, T.; Zhang, S.; Sun, A.; Spannenberg, A.; Fischer, C.; Buschmann, H.; Heller, D. Angew. Chem. 2005, 117, 1208-1212.
32. (v) Holz, J.; Zayas, O.; Jiao, H.; Baumann, W.; Spannenberg, A.; Monsees, A.; Riermeier, T. H.; Almena, J.; Kadyrov, R.; Börner, A. Chem. Eur. J. 2006, 12, 5001-5013.
33. Lagasse, F.; Kagan, H. B. Chem. Pharm. Bull. 2000, 48, 315-324.
34. Komarov, I. V.; Börner, A. Angew. Chem. 2001, 113, 1237-1240.
35. (a) Arnold, L. A.; Imobos, R.; Manoli, A.; de Vries, A. H. M.; Naasz, R.; Feringa, B. Tetrahedron 2000, 56, 2865-2878.
36. (b) 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. 2000, 122, 11539-11540.
37. (c) Minnaard, A. J.; van den Berg, M.; Schudde, E. P.; van Esch, J.; de Vries, A. H. M.; de Vries, J. G.; Feringa, B. Chim. Oggi 2001, 19, 12-13.
38. (d) Peña, D.; Minnaard, A. J.; de Vries, J. G.; Feringa, B. L. J. Am. Chem. Soc. 2002, 124, 14552-14553.
39. (e) van den Berg, M.; Haak, R. M.; Minnaard, A. J.; de Vries, A. H. M.; de Vries, J. G.; Feringa, B. L.; Adv. Synth. Catal. 2002, 344, 1003-1007.
40. (f) van den Berg, M.; Minnaard, A. J.; Haak, R. M.; Leeman, M.; Schudde, E. P.; Meetsma, A.; Feringa, B. L.; de Vries, A. H. M.; Maljaars, C. E. P.; Willans, C. E.; Hyett, D.; Boogers, J. A. F.; Henderickx, H. J. W.; de Vries, J. G. Adv. Synth. Catal. 2003, 345, 308-323.
41. (g) Peña, D.; Minnaard, A. J.; de Vries, A. H. M.; de Vries, J. G.; Feringa, B. L.; Org. Lett. 2003, 5, 475-478.
42. (h) Jiang, X.; van den Berg, M.; Minnaard, A. J.; Feringa, B.; de Vries, J. G. Tetrahedron: Asymmetry 2004, 15, 2223-2229.
43. (i) Eelkema, R.; van Delden, R. A.; Feringa, B. L. Angew. Chem., Im. Ed. 2004, 43, 5013-5016.
44. (j) Duursma, A.; Boiteau, J.-G.; Lefort, L.; Boogers, J. A. F.; de Vries, A. H. M.; de Vries, J. G.; Minnaard, A. J.; Feringa, B. L. J. Org. Chem. 2004, 69, 8045-8052.
45. (k) Lefort, L.; Boogers, J. A. F.; de Vries, A. H. M.; de Vries, J. G. Org. Lett. 2004, 6, 1733-1735.
46. (l) Bernsmann, H.; van den Berg, M.; Hoen, R.; Minnaard, A. J.; Mehler, G.; Reetz, M. T.; de Vries, J. G.; Feringa, B. L. J. Org. Chem. 2005, 70, 943-951.
47. (a) Reetz, M. T.; Sell, T. Tetrahedron Lett. 2000, 41, 6333-6336.
48. (b) Reetz, M. T.; Mehler, G. Angew. Chem., Int. Ed. 2000, 39, 3889-3891.
49. (c) Reetz, M. T.; Mehler, G.; Meiswinkel, G.; Sell, T. Tetrahedron Lett. 2002, 43, 7941-7493.
50. (d) Reetz, M. T.; Mehler, G.; Meiswinkel, G.; Sell, T. Angew. Chem., Int. Ed. 2003, 42, 790-793.
51. (e) Reetz, M. T.; Mehler, G. Tetrahedron Lett. 2003, 44, 4593-4596.
52. (f) Reetz, M. T.; Mehler, G.; Meiswinkel, A. Tetrahedron: Asymmetry 2004, 15, 2165-2167.
53. (g) Reetz, M. T.; Li, X. G. Tetrahedron 2004, 60, 9709-9714.
54. (h) Reetz, M. T.; Ma, J.-A.; Goddard, R. Angew. Chem., Int. Ed. 2005, 44, 412-414.
55. (i) Reetz, M. T.; Fu, Y.; Meiswinkel, A. Angew. Chem. 2006, 118, 1440-1443.
56. (a) Claver, C.; Fernandez, E.; Gillon, A.; Heslop, K.; Hyett, D. J.; Martorell, A.; Orpen, A. G.; Pringle, P. G. Chem. Commun. 2000, 961-962.
57. (b) Martorell, A.; Naasz, R.; Feringa, B. L.; Pringle, P. G. Tetrahedron: Asymmetry 2001, 12, 2497-2499.
58. (a) Hu, A.-G.; Fu, Y.; Xie, J.-H.; Zhou, H.; Wang, L.-X.; Zhou, Q.-L. Angew. Chem. 2002, 114, 2454-2456.
59. (b) Fu, Y.; Guo, X.-X.; Zhu, S.-F.; Hu, A.-G.; Xie, J.-H.; Zhou, Q.-L. J. Org. Chem. 2004, 69, 4648-4655.
60. (c) Fu, Y.; Hou, G.-H.; Xie, J.-H.; Xing, L.; Wang, L.-X.; Zhou, Q.-L. J. Org. Chem. 2004, 69, 8157-8160.
61. For other monodentate system see also: (a) Jerphagnon, T.; Renaud, L.-L.; Demonchauc, P.; Ferreira, A.; Bruneau, C. Adv. Synth. Catal. 2004, 346, 33-36.
62. (b) Bilenko, V.; Spannenberg, A.; Baumann, W.; Komarov, I.; Börner, A. Tetrahedron: Asymmetry 2006, 17, 2082-2087.
63. (a) Gladiali, S.; Dore, A.; Fabbri, D.; De Lucchi, O.; Manassero, M. Tetrahedron: Asymmmetry 1994, 5, 511-514.
64. (b) Gladiali, S.; Dore, A.; Fabbri, D.; De Lucchi, O.; Valle, G. J. Org. Chem. 1994, 59, 6363-6371.
65. (c) Gladiali, S.; Frabbi, D. Chem. Ber./Rec. Trav. Chim. Pays Bas. 1997, 130, 543-554.
66. (d) Charruault, L.; Michelet, V.; Taras, R.; Gladiali, S.; Genêt, J.-P. Chem. Commun. 2004, 850-851.
67. (e) Zanoni, G.; Gladiali, S.; Marchetti, A.; Piccinini, P.; Tredici, I.; Vidari, G. Angew. Chem., Int. Ed. 2004, 43, 846-849.
68. (f) Alberico, E.; Nieddu, I.; Taras, R.; Gladiali, S. Helv. Chim. Acta 2006, 89, 1716-1729.
69. (a) Chi, Y.; Zhang, X. Tetrahedron Lett. 2002, 43, 4849-4852.
70. (b) Tang, W.; Wang, W.; Chi, Y.; Zhang, X. Angew. Chem., Int. Ed. 2003, 42, 3506-3509.
71. (c) Chi, Y.; Zhou, Y.-G.; Zhang, X. J. Org. Chem. 2003, 68, 4120-4122.
72. (d) Xiao, D.; Zhang, X. Angew. Chem., Int. Ed. 2001, 40, 3425-3428.
73. (e) Xiao, D.; Zhang, Z.; Zhang, X. Org. Lett. 1999, 1, 1679-1681.
74. (a) Junge, K.; Oehme, G.; Monsees, A.; Riermeier, T.; Dingerdissen, U.; Beller, M. Tetrahedron Lett. 2002, 43, 4977-4980.
75. (b) Junge, K.; Oehme, G.; Monsees, A.; Riermeier, T.; Dingerdissen, U.; Beller, M. J. Organomet. Chem. 2003, 675, 91-96.
76. (c) Junge, K.; Hagemann, B.; Enthaler, S.; Spannenberg, A.; Michalik, M.; Oehme, G.; Monsees, A.; Riermeier, T.; Beller, M. Tetrahedron: Asymmetry 2004, 15, 2621-2631.
77. (d) Junge, K.; Hagemann, B.; Enthaler, S.; Oehme, G.; Michalik, M.; Monsees, A.; Riermeier, T.; Dingerdissen, U.; Beller, M. Angew. Chem. 2004, 116, 5176-5179;
78. Angew. Chem., Int. Ed. 2004, 43, 5066-5069.
79. (e) Hagemann, B.; Junge, K.; Enthaler, S.; Michalik, M.; Riermeier, T.; Monsees, A.; Beller, M. Adv. Synth. Catal. 2005, 347, 1978-1986.
80. (f) Enthaler, S.; Hagemann, B.; Junge, K.; Erre, G.; Beller, M. Eur. J. Org. Chem. 2006, 2912-2917.
81. (a) Wurz, R. P.; Fu, G. C. J. Am. Chem. Soc. 2005, 127, 12234-12235.
82. (b) Vedejs, E.; Daugulis, O.; Diver, S. T. J. Org. Chem. 1996, 61, 430-431.
83. (c) Wilson, J. E.; Fu, G. C. Angew. Chem., Int. Ed. 2006, 45, 1426-1429.
84. The ligands Ph-BINEPINE (6a) and t-Bu-BINEPINE (6i) are commercially available by Degussa DHC (Degussa Homogeneous Catalysis, Rodenbacher Chaussee 4, building 097, 63457 Haunau (Wolfgang), Germany, (www.creavis.com/site_dhc/de/default.cfm)) with the product names catASium KPh (6a) and catASium KtB (6i).
85. Optically pure 2,2′-binaphthol is available on large scale from RCA (Reuter Chemische Apparatebau KG), Engesserstr. 4, 79108 Freiburg, Germany.
86. The synthesis of 2,2′-bistriflate-1,1′-binaphthyl (1.2 mol, 615 g, 92%) and 2,2′-dimethyl-1,1′-binaphthyl (0.74 mol, 201 g, 96%) was carried out in large scale by the group of Zhang (See ref 11b).
87. Institute of Automation (IAT), Richard Wagner Str. 31/ H. 8,18119 Rostock-Warnemünde, Germany.
88. The hydrogenation performed in ethanol and 2-propanol led exclusively to product 7. No transesterification was observed.
89. In the case of toluene we assume an inhibition of the catalyst by the solvent, due to the formation of catalytical inactive rhodium-arene complexes. Heller, D.; Drexler, H.-J.; Spannenberg, A.; Heller, B.; You, J.; Baumann, W. Angew. Chem., Int. Ed. 2002, 41, 777-780.
90. Tsukamoto, M.; Yoshimura, M.; Tsuda, K.; Kitamura, M. Tetrahedron 2006, 62, 5448-5453.
91. Hu, X.-P.; Zheng, Z. Org. Lett. 2005, 7, 419-422.
92. Jerphagnon, T.; Renaud, J.-L.; Demonchaux, P.; Ferreira, A.; Bruneau, C. Tetrahedron: Asymmetry 2003, 14, 1973-1977.
93. Buschmann, H.; Scharf, K-D.; Hoffmann, N.; Esser, P. Angew. Chem. 1991, 103, 480-518.
94. (a) Girard, C.; Kagan, H. B.; Angew. Chem. 1998, 110, 3088-3127.
95. (b) Faller, J. W.; Parr, J. J. Am. Chem. Soc. 1993, 115, 804-805.
96. Tang, W.; Wu, S.; Zhang, X. J. Am. Chem. Soc. 2003, 125, 9570-9571.
97. (a) Reetz, M. T.; Li, X. Angew. Chem., Int. Ed. 2005, 44, 2959-2962.
98. (b) Reetz, M. T.; Li, X. Angew. Chem., Int. Ed. 2005, 44, 2962-2964.
99. (a) Duursma, A.; Hoen, R.; Schuppan, J.; Hulst, R.; Minnaard, A. J.; Feringa, B. L. Org. Lett. 2003, 5, 3111-3113.
100. (b) Duursma, A.; Peña, D.; Minnaard, A. J.; Feringa, B. L. Tetrahedron: Asymmetry 2005, 16, 1901-1904.
101. (c) Pẽa, D.; Minnaard, A. J.; Boogers, J. A. F.; de Vries, A. H. M.; Feringa, B. L. Org. Biomol. Chem. 2003, 1, 1087-1089.
102. (a) Monti, C.; Gennari, C.; Piarulli, U.; de Vries, J. G.; de Vries, A. H. M.; Lefort, L. Chem. Eur. J. 2005, 11, 6701-6717.
103. (b) Ding, K.; Du, H.; Yuan, Y.; Long, J. Chem. Eur. J. 2004, 10, 2872-2884.