Mono- versus bidentate ligands in rhodium-catalyzed asymmetric hydrogenation. A comparative rate study

Organic Letters

Volumn 5, Issue 4, 2003, Pages 475-478

  Peña, Diego ^a   Minnaard, Adriaan J ^a   De Vries, André H M ^b   De Vries, Johannes G ^b   Feringa, Ben L ^a  

^a UNIVERSITY OF GRONINGEN   (Netherlands)

^b DSM RESEARCH   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVE; LIGAND; MONODENTATE PHOSPHORAMIDITE; PHOSPHINE DERIVATIVE; PHOSPHORUS DERIVATIVE; RHODIUM; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC CATALYSIS; CHIRALITY; COMPARATIVE STUDY; ENANTIOSELECTIVITY; HYDROGENATION;

EID: 0012824998     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol027457t     Document Type: Article

References (49)

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19. For other recent examples: (a) Reetz, M. T.; Sell, T. Tetrahedron Lett. 2000, 41, 6333. (b) Chen, W.; Xiao, J. Tetrahedron Lett. 2001, 42, 2897. (c) Zeng, Q.; Liu, H.; Cui, X.; Mi, A.; Jiang, Y.; Li, X.; Choi, M. C. K.; Chan, A. S. C. Tetrahedron: Asymmetry 2002, 13, 115. (d) Junge, K.; Oehme, G.; Monsees, A.; Riermeier, T.; Dingerdissen, U.; Beller, M. Tetrahedron Lett. 2002, 43, 4977. (e) Fu, Y.; Xie, J.-H.; Hu, A.-G.; Zhou, H.; Wang, L.-X.; Zhou, Q.-L. Chem. Commun. 2002, 480. (f) Jia, X.; Guo, R.; Li, X.; Yao, X.; Chan, A. S. C. Tetrahedron Lett. 2002, 43, 5541. (g) Hu, A.-G.; Fu, Y.; Xie, J.-H.; Zhou, H.; Wang, L.-X.; Zhou, Q.-L. Angew. Chem., Int. Ed. 2002, 41, 2348. (h) 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. (i) Guillen, F.; Rivard, M.; Toffano, M.; Legros, J.-Y.; Daran J.-C.; Fiaud, J.-C. Tetrahedron 2002, 58, 5895. (j) 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, 1.
20. For other recent examples: (a) Reetz, M. T.; Sell, T. Tetrahedron Lett. 2000, 41, 6333. (b) Chen, W.; Xiao, J. Tetrahedron Lett. 2001, 42, 2897. (c) Zeng, Q.; Liu, H.; Cui, X.; Mi, A.; Jiang, Y.; Li, X.; Choi, M. C. K.; Chan, A. S. C. Tetrahedron: Asymmetry 2002, 13, 115. (d) Junge, K.; Oehme, G.; Monsees, A.; Riermeier, T.; Dingerdissen, U.; Beller, M. Tetrahedron Lett. 2002, 43, 4977. (e) Fu, Y.; Xie, J.-H.; Hu, A.-G.; Zhou, H.; Wang, L.-X.; Zhou, Q.-L. Chem. Commun. 2002, 480. (f) Jia, X.; Guo, R.; Li, X.; Yao, X.; Chan, A. S. C. Tetrahedron Lett. 2002, 43, 5541. (g) Hu, A.-G.; Fu, Y.; Xie, J.-H.; Zhou, H.; Wang, L.-X.; Zhou, Q.-L. Angew. Chem., Int. Ed. 2002, 41, 2348. (h) 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. (i) Guillen, F.; Rivard, M.; Toffano, M.; Legros, J.-Y.; Daran J.-C.; Fiaud, J.-C. Tetrahedron 2002, 58, 5895. (j) 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, 1.
21. For other recent examples: (a) Reetz, M. T.; Sell, T. Tetrahedron Lett. 2000, 41, 6333. (b) Chen, W.; Xiao, J. Tetrahedron Lett. 2001, 42, 2897. (c) Zeng, Q.; Liu, H.; Cui, X.; Mi, A.; Jiang, Y.; Li, X.; Choi, M. C. K.; Chan, A. S. C. Tetrahedron: Asymmetry 2002, 13, 115. (d) Junge, K.; Oehme, G.; Monsees, A.; Riermeier, T.; Dingerdissen, U.; Beller, M. Tetrahedron Lett. 2002, 43, 4977. (e) Fu, Y.; Xie, J.-H.; Hu, A.-G.; Zhou, H.; Wang, L.-X.; Zhou, Q.-L. Chem. Commun. 2002, 480. (f) Jia, X.; Guo, R.; Li, X.; Yao, X.; Chan, A. S. C. Tetrahedron Lett. 2002, 43, 5541. (g) Hu, A.-G.; Fu, Y.; Xie, J.-H.; Zhou, H.; Wang, L.-X.; Zhou, Q.-L. Angew. Chem., Int. Ed. 2002, 41, 2348. (h) 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. (i) Guillen, F.; Rivard, M.; Toffano, M.; Legros, J.-Y.; Daran J.-C.; Fiaud, J.-C. Tetrahedron 2002, 58, 5895. (j) 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, 1.
22. For other recent examples: (a) Reetz, M. T.; Sell, T. Tetrahedron Lett. 2000, 41, 6333. (b) Chen, W.; Xiao, J. Tetrahedron Lett. 2001, 42, 2897. (c) Zeng, Q.; Liu, H.; Cui, X.; Mi, A.; Jiang, Y.; Li, X.; Choi, M. C. K.; Chan, A. S. C. Tetrahedron: Asymmetry 2002, 13, 115. (d) Junge, K.; Oehme, G.; Monsees, A.; Riermeier, T.; Dingerdissen, U.; Beller, M. Tetrahedron Lett. 2002, 43, 4977. (e) Fu, Y.; Xie, J.-H.; Hu, A.-G.; Zhou, H.; Wang, L.-X.; Zhou, Q.-L. Chem. Commun. 2002, 480. (f) Jia, X.; Guo, R.; Li, X.; Yao, X.; Chan, A. S. C. Tetrahedron Lett. 2002, 43, 5541. (g) Hu, A.-G.; Fu, Y.; Xie, J.-H.; Zhou, H.; Wang, L.-X.; Zhou, Q.-L. Angew. Chem., Int. Ed. 2002, 41, 2348. (h) 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. (i) Guillen, F.; Rivard, M.; Toffano, M.; Legros, J.-Y.; Daran J.-C.; Fiaud, J.-C. Tetrahedron 2002, 58, 5895. (j) 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, 1.
23. For other recent examples: (a) Reetz, M. T.; Sell, T. Tetrahedron Lett. 2000, 41, 6333. (b) Chen, W.; Xiao, J. Tetrahedron Lett. 2001, 42, 2897. (c) Zeng, Q.; Liu, H.; Cui, X.; Mi, A.; Jiang, Y.; Li, X.; Choi, M. C. K.; Chan, A. S. C. Tetrahedron: Asymmetry 2002, 13, 115. (d) Junge, K.; Oehme, G.; Monsees, A.; Riermeier, T.; Dingerdissen, U.; Beller, M. Tetrahedron Lett. 2002, 43, 4977. (e) Fu, Y.; Xie, J.-H.; Hu, A.-G.; Zhou, H.; Wang, L.-X.; Zhou, Q.-L. Chem. Commun. 2002, 480. (f) Jia, X.; Guo, R.; Li, X.; Yao, X.; Chan, A. S. C. Tetrahedron Lett. 2002, 43, 5541. (g) Hu, A.-G.; Fu, Y.; Xie, J.-H.; Zhou, H.; Wang, L.-X.; Zhou, Q.-L. Angew. Chem., Int. Ed. 2002, 41, 2348. (h) 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. (i) Guillen, F.; Rivard, M.; Toffano, M.; Legros, J.-Y.; Daran J.-C.; Fiaud, J.-C. Tetrahedron 2002, 58, 5895. (j) 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, 1.
24. For other recent examples: (a) Reetz, M. T.; Sell, T. Tetrahedron Lett. 2000, 41, 6333. (b) Chen, W.; Xiao, J. Tetrahedron Lett. 2001, 42, 2897. (c) Zeng, Q.; Liu, H.; Cui, X.; Mi, A.; Jiang, Y.; Li, X.; Choi, M. C. K.; Chan, A. S. C. Tetrahedron: Asymmetry 2002, 13, 115. (d) Junge, K.; Oehme, G.; Monsees, A.; Riermeier, T.; Dingerdissen, U.; Beller, M. Tetrahedron Lett. 2002, 43, 4977. (e) Fu, Y.; Xie, J.-H.; Hu, A.-G.; Zhou, H.; Wang, L.-X.; Zhou, Q.-L. Chem. Commun. 2002, 480. (f) Jia, X.; Guo, R.; Li, X.; Yao, X.; Chan, A. S. C. Tetrahedron Lett. 2002, 43, 5541. (g) Hu, A.-G.; Fu, Y.; Xie, J.-H.; Zhou, H.; Wang, L.-X.; Zhou, Q.-L. Angew. Chem., Int. Ed. 2002, 41, 2348. (h) 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. (i) Guillen, F.; Rivard, M.; Toffano, M.; Legros, J.-Y.; Daran J.-C.; Fiaud, J.-C. Tetrahedron 2002, 58, 5895. (j) 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, 1.
25. For other recent examples: (a) Reetz, M. T.; Sell, T. Tetrahedron Lett. 2000, 41, 6333. (b) Chen, W.; Xiao, J. Tetrahedron Lett. 2001, 42, 2897. (c) Zeng, Q.; Liu, H.; Cui, X.; Mi, A.; Jiang, Y.; Li, X.; Choi, M. C. K.; Chan, A. S. C. Tetrahedron: Asymmetry 2002, 13, 115. (d) Junge, K.; Oehme, G.; Monsees, A.; Riermeier, T.; Dingerdissen, U.; Beller, M. Tetrahedron Lett. 2002, 43, 4977. (e) Fu, Y.; Xie, J.-H.; Hu, A.-G.; Zhou, H.; Wang, L.-X.; Zhou, Q.-L. Chem. Commun. 2002, 480. (f) Jia, X.; Guo, R.; Li, X.; Yao, X.; Chan, A. S. C. Tetrahedron Lett. 2002, 43, 5541. (g) Hu, A.-G.; Fu, Y.; Xie, J.-H.; Zhou, H.; Wang, L.-X.; Zhou, Q.-L. Angew. Chem., Int. Ed. 2002, 41, 2348. (h) 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. (i) Guillen, F.; Rivard, M.; Toffano, M.; Legros, J.-Y.; Daran J.-C.; Fiaud, J.-C. Tetrahedron 2002, 58, 5895. (j) 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, 1.
26. For other recent examples: (a) Reetz, M. T.; Sell, T. Tetrahedron Lett. 2000, 41, 6333. (b) Chen, W.; Xiao, J. Tetrahedron Lett. 2001, 42, 2897. (c) Zeng, Q.; Liu, H.; Cui, X.; Mi, A.; Jiang, Y.; Li, X.; Choi, M. C. K.; Chan, A. S. C. Tetrahedron: Asymmetry 2002, 13, 115. (d) Junge, K.; Oehme, G.; Monsees, A.; Riermeier, T.; Dingerdissen, U.; Beller, M. Tetrahedron Lett. 2002, 43, 4977. (e) Fu, Y.; Xie, J.-H.; Hu, A.-G.; Zhou, H.; Wang, L.-X.; Zhou, Q.-L. Chem. Commun. 2002, 480. (f) Jia, X.; Guo, R.; Li, X.; Yao, X.; Chan, A. S. C. Tetrahedron Lett. 2002, 43, 5541. (g) Hu, A.-G.; Fu, Y.; Xie, J.-H.; Zhou, H.; Wang, L.-X.; Zhou, Q.-L. Angew. Chem., Int. Ed. 2002, 41, 2348. (h) 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. (i) Guillen, F.; Rivard, M.; Toffano, M.; Legros, J.-Y.; Daran J.-C.; Fiaud, J.-C. Tetrahedron 2002, 58, 5895. (j) 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, 1.
27. For a recent review, see: Komarov, I. V.; Börner, A. Angew. Chem., Int. Ed. 2001, 40, 1197.
28. Now commercially available through Strem Chemicals. See also: van den Berg, M.; Minnaard, A. J.; de Vries, J. G.; Feringa, B. L. (DSM N. V.). World Patent WO 02/04466, 2002.
29. Hulst, R.; de Vries, N. K.; Feringa, B. L. Tetrahedron: Asymmetry 1994, 5, 699.
30. Peña, D.; Minnaard, A.; de Vries, J. G.; Feringa, B. L. J. Am. Chem. Soc. 2002, 124, 14552.
31. 2.
32. The ee obtained using 1 as a ligand in the Rh-catalyzed hydrogenation of 7 is constant when increasing the hydrogen pressure (at least up to 60 bar), while it is enhanced when performing the reaction at lower temperatures (0 vs 25 °C; see ref 5d). On the contrary, in the case of ligand 2, the ee drops when increasing the hydrogen pressure or when decreasing the reaction temperature.
33. Burk, M. J. J. Am. Chem. Soc. 1991, 113, 8518.
34. Pye, P. J.; Rossen, K.; Reamer, R. A.; Tsou, N. N.; Volante, R. P.; Reider, P. J. J. Am. Chem. Soc. 1997, 119, 6207.
35. Togni, A.; Breutel, C.; Schnyder, A.; Spindler, F.; Landert, H.; Tijani, A. J. Am. Chem. Soc. 1994, 116, 4062.
36. Heller et al. have extensively reported on these issues. For instance, see: (a) Börner, A.; Heller, D. Tetrahedron Lett. 2001, 42, 223. (b) Drexler, H.-J.; Baumann, W.; Spannenberg, A.; Fischer, C.; Heller, D. J. Organomet. Chem. 2001, 621, 89.
37. Heller et al. have extensively reported on these issues. For instance, see: (a) Börner, A.; Heller, D. Tetrahedron Lett. 2001, 42, 223. (b) Drexler, H.-J.; Baumann, W.; Spannenberg, A.; Fischer, C.; Heller, D. J. Organomet. Chem. 2001, 621, 89.
38. 4 and 2 equiv (monodentates) or 1 equiv (bidentates) of the ligand were dissolved in DCM (20 mM). After the mixture was stirred under argon at room temperature for 15 min, volatiles were removed and the appropriate solvent was added (1 mM in the case of 2 due to the low solubility of the complex; 20 mM in the rest).
39. Total purge time was 20 min.
40. In our hands, preliminary runs had shown the superiority of DuPhos over PhanePhos and JosiPhos in the hydrogenation of 7 under our standard conditions. See Supporting Information for details.
41. Higher enantioselectivities in the hydrogenation of 7 were reported for these ligands under different conditions: 1, 98% ee (ref 5d); 4, 98% ee (ref 13).
42. Heller, D.; Drexler, H.-J.; You, J.; Baumann, W.; Drauz, K.; Krimmer, H.-P.; Börner, A. Chem. Eur. J. 2002, 8, 5196.
43. Tang, W.; Zhang, X. Org. Lett. 2002, 4, 4169 and refs cited therein.
44. 4 and 2 equiv (monodentates) or 1 equiv (bidentates) of the ligand were dissolved in DCM (20 mM). After the mixture was stirred under argon at room temperature for 15 min, volatiles were removed and DCM (1-3, 20 mM) or MeOH (4-6, 20 mM) was added.
45. With ligands 1-3, the preformed precatalysts were added in DCM solution, therefore the actual composition of the solvent was 4:1 i-PrOH/DCM.
46. (a) MeOH is the best solvent for the hydrogenation of (Z)-β-dehydroamino acid derivatives using DuPhos reported so far. See:
47. (b) Heller, D.; Holz, J.; Drexler, H.-J.; Lang, J.; Drauz, K.; Krimmer, H.-P.; Börner, A. J. Org. Chem. 2001, 66, 6816.
48. Among these ligands, only 2 (ref 10) and 4 (ref 25b) have been previously reported in the asymmetric hydrogenation of β-dehydroamino acid derivatives.
49. 2 pressure. Actually, at 1 bar, 87% ee can be reached with this ligand (see ref 25b).