Design of phosphorus ligands with deep chiral pockets: Practical Synthesis of chiral β-arylamines by asymmetric hydrogenation

Angewandte Chemie - International Edition

Volumn 52, Issue 15, 2013, Pages 4235-4238

  Liu, Guodu ^a   Liu, Xiangqian ^a   Cai, Zhihua ^a   Jiao, Guangjun ^a   Xu, Guangqing ^a   Tang, Wenjun ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

aryl enamides; asymmetric catalysis; homogeneous catalysis; hydrogenation; phosphorus ligands

Indexed keywords

ARYL AMINES; ASYMMETRIC CATALYSIS; ASYMMETRIC HYDROGENATION; ENAMIDES; HOMOGENEOUS CATALYSIS; PHOSPHORUS LIGANDS; RHODIUM-CATALYZED; TURNOVER NUMBER;

CATALYSIS; HYDROGENATION; PHOSPHORUS; REACTION KINETICS;

LIGANDS;

AMINE; LIGAND; ORGANOPHOSPHORUS COMPOUND;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; HYDROGENATION; SYNTHESIS;

AMINES; HYDROGENATION; LIGANDS; MOLECULAR STRUCTURE; ORGANOPHOSPHORUS COMPOUNDS;

EID: 84875869395     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201300646     Document Type: Article

References (47)

1. Comprehensive Asymmetric Catalysis (Eds.:, E.N. Jacobsen, A. Pfaltz, H. Yamamoto,), Springer, Berlin, 1999
2. Asymmetric Catalysis on Industrial Scale: Challenges, Approaches and Solutions (Eds.:, H.-U. Blaser, E. Schmidt,), Wiley-VCH, Weinheim, 2004
3. W. Tang, X. Zhang, Chem. Rev. 2003, 103, 3029
4. J.-H. Xie, S.-F. Zhu, Q.-L. Zhou, Chem. Rev. 2011, 111, 1713
5. K. Gopalaiah, H. B. Kagan, Chem. Rev. 2011, 111, 4599
6. D.-S. Wang, Q.-A. Chen, S.-M. Lu, Y.-G. Zhou, Chem. Rev. 2012, 112, 2557.
7. R. Noyori, Asymmetric Catalysis in Organic Synthesis, Wiley, New York, 1994.
8. M. J. Burk, Acc. Chem. Res. 2000, 33, 363.
9. W. Tang, X. Zhang, Angew. Chem. 2002, 114, 1682
10. Angew. Chem. Int. Ed. 2002, 41, 1612.
11. G. Bringmann, T. Gulder, T. A. M. Gulder, M. Breuning, Chem. Rev. 2011, 111, 563
12. G. Bringmann, P. Frank, in Alkaloids, Vol.46, Academic Press, New York, 1995, p. 127
13. K. P. Manfredi, J. W. Blunt, J. H. Cardellina II, J. B. McMahon, L. L. Pannell, G. M. Cragg, J. Med. Chem. 1991, 34, 3402
14. Y. F. Hallock, K. P. Manfredi, J. R. Dai, J. H. Cardellina II, R. J. Gulakowski, J. B. McMahon, M. Schaffer, M. Stahl, K. P. Gulden, G. Bringmann, G. Francois, M. R. Boyd, J. Nat. Prod. 1997, 60, 677.
15. S. H. Snyder, K. M. Tayler, Science 1970, 168, 1487
16. C. G. Roehrborn, P. Siami, J. Barkin, R. Damião, K. Major-Walker, B. Morrill, F. Montorsi, J. Urol. 2008, 179, 616
17. M. Sano, C. Ernesto, R. C. Thomas, M. R. N. Klauber, N. Engl. J. Med. 1997, 336, 1216
18. B. Barnes, Formoterol, A New Generation of Beta-2-agonist, Hogrefe and Huber Pub., Toronto, 1991
19. D. Q. Pharm, A. Nogid, Clin. Ther. 2008, 30, 813
20. M. Yoshida, Y. Homma, K. Kawabe, Expert Opin. Invest. Drugs 2007, 16, 1955.
21. Chiral Amine Synthesis: Methods, Developments and Applications (Ed.:, T.C. Nugent,), Wiley-VCH, Weinheim, 2010.
22. J. Chen, W. Zhang, H. Geng, W. Li, G. Hou, A. Lei, X. Zhang, Angew. Chem. 2009, 121, 814
23. Angew. Chem. Int. Ed. 2009, 48, 800.
24. S.-F. Zhu, T. Liu, S. Yang, S. Song, Q.-L. Zhou, Tetrahedron 2012, 68, 7685.
25. D. M. Tschaen, L. Abramson, D. Cai, R. Desmond, U.-H. Dolling, L. Frey, S. Karady, Y.-J. Shi, T. R. Verhoeven, J. Org. Chem. 1995, 60, 4324
26. P. Dupau, P. LeGendre, C. Bruneau, P. H. Dixneuf, Synlett 1999, 1832
27. X.-B. Jiang, L. Lefort, A. H. H. H. deVries, P. W. N. M. vanLeeuwen, J. G. deVries, J. N. H. Reek, Angew. Chem. 2006, 118, 1245
28. Angew. Chem. Int. Ed. 2006, 45, 1223.
29. J. L. Renaud, P. Dupau, A.-E. Hay, M. Guingouain, P. H. Dixneuf, C. Bruneau, Adv. Synth. Catal. 2003, 345, 230
30. A. Beliaev, J. Wahnon, D. Russo, Org. Process Res. Dev. 2012, 16, 704.
31. For Beckmann rearrangement of ketoximes, see
32. R. Brettle, S. M. Shibib, K. J. Wheeler, J. Chem. Soc. Perkin Trans. 1 1985, 831; for reductive acylation of ketoximes, see
33. M. J. Burk, G. Casy, N. B. Johnson, J. Org. Chem. 1998, 63, 6084
34. G. Zhu, A. L. Casalnuovo, J. Org. Chem. 1998, 63, 8100
35. W. Tang, A. Capacci, M. Sarvestani, X. Wei, N. K. Yee, C. H. Senanayake, J. Org. Chem. 2009, 74, 9528
36. Z. Guan, Z. Zhang, Z. Ren, Y. Wang, X. Zhang, J. Org. Chem. 2011, 76, 339; for palladium-catalyzed cross-coupling, see
37. D. J. Wallace, D. J. Klauber, C.-Y. Chen, R. P. Volante, Org. Lett. 2003, 5, 4749.
38. N. M. Laso, B. Quiclet-Sire, S. Z. Zard, Tetrahedron Lett. 1996, 37, 1605.
39. W. Tang, B. Qu, A. G. Capacci, S. Rodriguez, X. Wei, N. Haddad, B. Narayanan, S. Ma, N. Grinberg, N. K. Yee, S. Krishnamurthy, C. H. Senanayake, Org. Lett. 2010, 12, 176
40. D. R. Fandrick, K. R. Fandrick, J. T. Reeves, Z. Tan, W. Tang, A. G. Capacci, S. Rodriguez, J. J. Song, H. Lee, N. K. Yee, C. H. Senanayake, J. Am. Chem. Soc. 2010, 132, 7600.
41. M. Yasutake, I. D. Gridnev, N. Higashi, T. Imamoto, Org. Lett. 2001, 3, 1701
42. I. D. Gridnev, M. Yasutake, N. Higashi, T. Imamoto, J. Am. Chem. Soc. 2001, 123, 5268.
43. I. D. Gridnev, N. Higashi, K. Asakura, T. Imamoto, J. Am. Chem. Soc. 2000, 122, 7183
44. I. D. Gridnev, N. Higashi, T. Imamoto, J. Am. Chem. Soc. 2000, 122, 10486
45. I. D. Gridnev, T. Imamoto, Organometallics 2001, 20, 545
46. I. D. Gridnev, T. Imamoto, Acc. Chem. Res. 2004, 37, 633
47. I. D. Gridnev, T. Imamoto, Chem. Commun. 2009, 7447.