A mild dihydrobenzooxaphosphole oxazoline/iridium catalytic system for asymmetric hydrogenation of unfunctionalized dialins

Angewandte Chemie - International Edition

Volumn 53, Issue 52, 2014, Pages 14428-14432

  Qu, Bo ^a   Samankumara, Lalith P ^a   Ma, Shengli ^a   Frick, Keith R ^a   Desrosiers, Jean Nicolas ^a   Rodriguez, Sonia ^a   Li, Zhibin ^a   Haddad, Nizar ^a   Han, Zhengxu S ^a   McKellop, Keith ^a   Pennino, Scott ^a   Grinberg, Nelu ^a   Gonnella, Nina C ^a   Song, Jinhua J ^a   Senanayake, Chris H ^a  

^a BOEHRINGER INGELHEIM PHARMACEUTICALS INC   (United States)

Author keywords

Asymmetric catalysis; Imines; Iridium; P,n ligands; Reduction

Indexed keywords

CATALYSIS; IRIDIUM; LIGANDS; NITROGEN COMPOUNDS; REDUCTION;

ASYMMETRIC CATALYSIS; ASYMMETRIC HYDROGENATION; ATMOSPHERE PRESSURE; HIGH ENANTIOSELECTIVITY; IMINE DERIVATIVES; IMINES; OXAZOLINE LIGANDS; P ,N LIGANDS;

HYDROGENATION;

HYDROGEN; IMINES; IRIDIUM; OXAZOLES;

CATALYSIS; CHEMISTRY; HYDROGENATION; MODELS, MOLECULAR; STEREOISOMERISM;

CATALYSIS; HYDROGEN; HYDROGENATION; IMINES; IRIDIUM; MODELS, MOLECULAR; OXAZOLES; STEREOISOMERISM;

EID: 84919683680     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201408929     Document Type: Article

References (36)

1. a) F. Zhang, S. Das, A. J. Walkinshaw, A. Casitas, M. Taylor, M. G. Suero, M. J. Gaunt, J. Am. Chem. Soc. 2014, 136, 8851-8854;
2. b) A. Volonterio, M. Zanda, Tetrahedron Lett. 2005, 46, 8723-8726.
3. a) F. Bohlmann, C. Zdero, H. Robinson, R. M. King, Phytochemistry 1979, 18, 1675-1680;
4. )W. M. Welch, A. R. Kraska, R. Sarges, B. K. Koe, J. Med. Chem. 1984, 27, 1508-1515;
5. c) Z. Xiao, K. F. Bastow, J. R. Vance, R. S. Sidwell, H.-K. Wang, M. S. Chen, Q. Shi, K.-H. Lee, J. Med. Chem. 2004, 47, 5140-5148;
6. d) E. Rasolofonjatovo, O. Provot, A. Hamze, J. Rodrigo, J. Bignon, J. Wdzieczak-Bakala, D. Desravines, J. Dubois, J.-D. Brion, M. Alami, Eur. J. Med. Chem. 2012, 52, 22-32.
7. a) S. Bell, B. Wüstenberg, S. Kaiser, F. Menges, T. Netscher, A. Pfaltz, Science 2006, 311, 642-644;
8. b) J. J. Verendel, O. Pàmies, M. Diéguez, P. G. Andersson, Chem. Rev. 2014, 114, 2130-2169;
9. c) X. Cui, K. Burgess, Chem. Rev. 2005, 105, 3272-3296.
10. D. H. Woodmansee, M.-A. Müller, M. Neuburger, A. Pfaltz, Chem. Sci. 2010, 1, 72-78.
11. R. D. Broene, S. L. Buchwald, J. Am. Chem. Soc. 1993, 115, 12569-12570.
12. a) M. G. Schrems, A. Pfaltz, Chem. Commun. 2009, 6210-6212;
13. b) A. Franzke, F. Voss, A. Pfaltz, Tetrahedron 2011, 67, 4358-4363.
14. B. Qu, L. P. Samankumara, J. Savoie, D. R. Fandrick, N. Haddad, X.Wei, S. Ma, H. Lee, S. Rodriguez, C. A. Busacca, et al., J. Org. Chem. 2014, 79, 993-1000.
15. a)W. Tang, B. Qu, A. G. Capacci, S. Rodriguez, X. Wei, N. Haddad, B. Narayanan, S. Ma, N. Grinberg, N. K. Yee, et al., Org. Lett. 2010, 12, 176-179;
16. b) Z. S. Han, N. Goyal, M. A. Herbage, J. D. Sieber, B. Qu, Y. Xu, Z. Li, J. T. Reeves, J.-N. Desrosiers, S. Ma, et al., J. Am. Chem. Soc. 2013, 135, 2474-2477.
17. I. Gallou, C. H. Senanayake, Chem. Rev. 2006, 106, 2843-2874.
18. a) A. K. Ghosh, P. Mathivanan, J. Cappiello, Tetrahedron: Asymmetry 1998, 9, 1-45;
19. b) F. Fache, E. Schulz, M. L. Tommasino, M. Lemaire, Chem. Rev. 2000, 100, 2159-2231.
20. J. R. Dunetz, Y. Xiang, A. Baldwin, J. Ringling, Org. Lett. 2011, 13, 5048-5051.
21. I.W. Davies, L. Gerena, N. Lu, R. D. Larsen, P. J. Reider, J. Org. Chem. 1996, 61, 9629-9630.
22. K. Naumann, G. Zon, K. Mislow, J. Am. Chem. Soc. 1969, 91, 2788-2789.
23. A. Lightfoot, P. Schnider, A. Pfaltz, Angew. Chem. Int. Ed. 1998, 37, 2897-2899; Angew. Chem. 1998, 110, 3047-3050.
24. T. B. Freedman, X. Cao, R. K. Dukor, L. A. Nafie, Chirality 2003, 15, 743-758.
25. C. A. Busacca, B. Qu, N. Grět, K. R. Fandrick, A. K. Saha, M. Marsini, D. Reeves, N. Haddad, M. Eriksson, J.-P. Wu, et al., Adv. Synth. Catal. 2013, 355, 1455-1463.
26. CCDC 1023264 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www. ccdc.cam.ac.uk/data-request/cif.
27. Gaussian 09 (Revision C.01), M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, et al., Gaussian, Inc., Wallingford CT, 2010.
28. a) Y. Fan, X. Cui, K. Burgess, M. B. Hall, J. Am. Chem. Soc. 2004, 126, 16688-16689;
29. b) T. L. Church, R. Rasmussen, P. G. Andersson, Organometallics 2010, 29, 6769-6781.
30. a) C. D. Nenitzescu, M. Avram, J. Am. Chem. Soc. 1950, 72, 3486-3490;
31. b) L. E. Miller, D. J. Mann, J. Am. Chem. Soc. 1951, 73, 45-48;
32. c) M. Crawford, V. R. Supanekar, J. Chem. Soc. C 1968, 2328-2332.
33. Only one literature report on the synthesis of 7 f is reported, but without characterization data: C. D. Zotto, J.Wehbe, D. Virieux, J.-M. Campagne, Synlett 2008, 2033-2035.
34. a) A. Trifonova, J. S. Diesen, P. G. Andersson, Chem. Eur. J. 2006, 12, 2318-2328;
35. )W.-J. Lu, Y.-W. Chen, X.-L. Hou, Adv. Synth. Catal. 2010, 352, 103-107.
36. Z. Han, Z. Wang, X. Zhang, K. Ding, Angew. Chem. Int. Ed. 2009, 48, 5345-5349; Angew. Chem. 2009, 121, 5449-5453.