Highly enantioselective Rh-catalysed hydrogenation of 1-alkyl vinyl esters using phosphine-phosphoramidite ligands

Chemistry - A European Journal

Volumn 19, Issue 40, 2013, Pages 13299-13303

  Konrad, Tina Maria ^a   Schmitz, Pascal ^a   Leitner, Walter ^a   Franciò, Giancarlo ^a  

^a RWTH AACHEN UNIVERSITY   (Germany)

Author keywords

asymmetric hydrogenation; chiral alcohols; enol esters; phosphine phosphoramidite ligands; rhodium

Indexed keywords

ALKYL ALCOHOLS; ASYMMETRIC HYDROGENATION; CATALYST LOADINGS; CHIRAL ALCOHOLS; ENANTIOSELECTIVE; ENOL ESTERS; PHOSPHORAMIDITE LIGANDS; ROOM TEMPERATURE;

CATALYSTS; ESTERIFICATION; ESTERS; HYDROGENATION; PHOSPHORUS COMPOUNDS; RHODIUM;

LIGANDS;

EID: 84884812350     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201303066     Document Type: Article

References (53)

1. Handbook of Homogeneous Hydrogenation, (Eds.:, J. G. de Vries, C. J. Elsevier,), Wiley-VCH, Weinheim, 2007
2. P. Etayo, A. Vidal-Ferran, Chem. Soc. Rev. 2013, 42, 728-754
3. H.-U. Blaser, B. Pugin, F. Spindler, Top. Organomet. Chem. 2012, 42, 65-102; special issue on hydrogenation
4. Acc. Chem. Res. 2008, 40, 1237-1419
5. W. Tang, X. Zhang, Chem. Rev. 2003, 103, 3029-3069.
6. J. Li, Y. Tang, Q. Wang, X. Li, L. Cun, X. Zhang, J. Zhu, L. Li, J. Deng, J. Am. Chem. Soc. 2012, 134, 18522-18525
7. M. Boukachabia, S. Zeror, J. Collin, J.-C. Fiaud, L. A. Zouioueche, Tetrahedron Lett. 2011, 52, 1485-1489
8. A. Schlatter, M. K. Kundu, W.-D. Woggon, Angew. Chem. 2004, 116, 6899-6902
9. Angew. Chem. Int. Ed. 2004, 43, 6731-6734.
10. N. Arai, T. Ohkuma, in Science of Synthesis Stereoselective Synthesis, Vol. 2 (Eds.:, J. G. De Vries, G. A. Molander, P. A. Evans,), Thieme, Stuttgart, 2011, pp. 9-57
11. T. Ohkuma, R. Noyori, Comprehensive Asymmetric Catalysis I-III, Vol. 1, Springer, Heidelberg, 1999, pp. 199-246
12. T. Ohkuma, R. Noyori, in Handbook of Homogeneous Hydrogenation, Vol. 3, (Eds.:, J. G. de Vries, C. J. Elsevier,), Wiley-VCH, Weinheim, 2007, pp. 1105-1116.
13. T. Okhuma, M. Koizumi, H. Doucet, T. Pham, M. Kozawa, K. Murata, E. Katayama, T. Yokozawa, T. Ikariya, R. Noyori, J. Am. Chem. Soc. 1998, 120, 13529
14. T. Ohkuma, M. Koizumi, K. Muñiz, G. Hilt, C. Kabuto, R. Noyori, J. Am. Chem. Soc. 2002, 124, 6508.
15. Q. Jiang, Y. Jiang, D. Xiao, P. Cao, X. Zhang, Angew. Chem. 1998, 110, 1203-1207
16. Angew. Chem. Int. Ed. 1998, 37, 1100-1103
17. T. Ohkuma, C. A. Sandoval, R. Strinivasan, Q. Lin, Y. Wei, K. Muñiz, R. Noyori, J. Am. Chem. Soc. 2005, 127, 8288.
18. S. De Wildeman, N. Sereinig, in Science of Synthesis Stereoselective Synthesis, Vol. 2 (Eds.:, J. G. de Vries, G. A. Molander, P. A. Evans,), Thieme, Stuttgart, 2011, pp. 133-208; for recent examples see
19. S. Leuchs, S. Na'amnieh, L. Greiner, Green Chem. 2013, 15, 167-176
20. S. Leuchs, T. Nonnen, D. Dechambre, S. Na'amnieh, L. Greiner, J. Mol. Catal. B 2013, 88, 52-59.
21. A. Berkessel, M. L. Sebastian-Ibarz, T. N. Müller, Angew. Chem. 2006, 118, 6717-6720
22. Angew. Chem. Int. Ed. 2006, 45, 6567-6570.
23. For hydrogenation of substituted enol carbamates see:, L. Panella, B. L. Feringa, J. G. de Vries, A. J. Minnaard, Org. Lett. 2005, 7, 4177-4180.
24. T. W. Liwosz, S. R. Chemler, J. Am. Chem. Soc. 2012, 134, 2020-2023.
25. L. J. Gooßen, J. Paetzold, D. Koley, Chem. Commun. 2003, 706-707.
26. Q. Jiang, D. Xiao, Z. Zhang, P. Cao, X. Zhang, Angew. Chem. 1999, 111, 578-580
27. Angew. Chem. Int. Ed. 1999, 38, 516-518.
28. S. Wu, W. Wang, W. Tang, M. Lin, X. Zhang, Org. Lett. 2002, 4, 4495-4497
29. Y. Liu, Z. Wang, K. Ding, Tetrahedron 2012, 68, 7581-7585
30. J. L. Nunez-Rico, P. Etayo, H. Fernandez-Perez, A. Vidal-Ferran, Adv. Synth. Catal. 2012, 354, 3025-3035.
31. U. Schmidt, J. Langner, B. Kirschbaum, C. Braun, Synthesis 1994, 1138-1140
32. G. Arena, G. Barreca, L. Carcone, E. Cini, G. Marras, H. G. Nedden, M. Rasparini, S. Roseblade, A. Russo, M. Taddei, A. Zanotti-Gerosa, Adv. Synth. Catal. 2003, 345, 1449-1454.
33. Y. Kuroki, D. Asada, Y. Sakamaki, K. Iseki, Tetrahedron Lett. 2000, 41, 4603-4607.
34. N. W. Boaz, Tetrahedron Lett. 1998, 39, 5505-5508.
35. M. T. Reetz, L. J. Gooßen, A. Meiswinkel, J. Paetzold, J. J. Feldthusen, Org. Lett. 2003, 5, 3099-3101.
36. P. Mamone, M. F. Grünberg, A. Fromm, B. A. Khan, L. J. Gooßen, Org. Lett. 2012, 14, 3716.
37. F. Boeda, T. Beneyton, C. Crevisy, Mini-Rev. Org. Chem. 2008, 5, 96-127
38. N. W. Boaz, J. A. Ponasik, in Phosphorus Ligands in Asymmetric Catalysis (Ed.:, A. Börner,), Wiley-VCH, Weinheim, 2008, pp. 453-476
39. J. Wassenaar, J. N. H. Reek, Org. Biomol. Chem. 2011, 9, 1704-1713.
40. G. Franciò, F. Faraone, W. Leitner, Angew. Chem. 2000, 112, 1486-1488
41. Angew. Chem. Int. Ed. 2000, 39, 1428-1430.
42. M. Eggenstein, A. Thomas, J. Theuerkauf, G. Franciò, W. Leitner, Adv. Synth. Catal. 2009, 351, 725-732.
43. G. Franciò, F. Faraone, W. Leitner, in Asymmetric Synthesis with Chemical and Biological Methods (Eds.:, D. Enders, K.-E. Jaeger,), Wiley-VCH, Weinheim, 2007, pp. 250-277
44. T. Pullmann, B. Engendahl, Z. Zhang, M. Hölscher, A. Zanotti-Gerosa, A. Dyke, G. Franciò, W. Leitner, Chem. Eur. J. 2010, 16, 7517-7526; for continuous flow asymmetric hydrogenation with QuinaPhos see
45. U. Hintermair, T. Hoefener, T. Pullmann, G. Franciò, W. Leitner, ChemCatChem 2010, 2, 150-154
46. U. Hintermair, G. Franciò, W. Leitner, Chem. Eur. J. 2013, 19, 4538-4547.
47. S. Burk, G. Franciò, W. Leitner, Chem. Commun. 2005, 3460-3462.
48. P. F. Hudrlik, A. M. Hudrlik, J. Org. Chem. 1973, 38, 4254-4258
49. B. C. Chary, S. Kim, J. Org. Chem. 2010, 75, 7928-7931.
50. N. W. Boaz, (Eastman Chemical Co., Kingsport, Tenneseee), EP872467 A1.
51. W. Tang, D. Liu, X. Zhang, Org. Lett. 2003, 5, 205-207
52. X. Zhang, K. Huang, G. Hou, B. Cao, X. Zhang, Angew. Chem. 2010, 122, 6565-6568
53. Angew. Chem. Int. Ed. 2010, 49, 6421-6424.