Diastereo- and enantioselective asymmetric hydrogenation of α-amido-β-keto phosphonates via dynamic kinetic resolution

Organic Letters

Volumn 15, Issue 1, 2013, Pages 72-75

  Tao, Xiaoming ^a   Li, Wanfang ^a   Li, Xiaoming ^a   Xie, Xiaomin ^a   Zhang, Zhaoguo ^a,b  

^a SHANGHAI JIAO TONG UNIVERSITY   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID; CERIUM; CERIUM CHLORIDE; ESTER; PHOSPHONIC ACID DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; HYDROGENATION; KINETICS; STEREOISOMERISM; SYNTHESIS;

AMINO ACIDS; CATALYSIS; CERIUM; ESTERS; HYDROGENATION; KINETICS; MOLECULAR STRUCTURE; ORGANOPHOSPHONATES; STEREOISOMERISM;

EID: 84874028737     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol303105d     Document Type: Article

References (57)

1. Dhawan, B.; Redmore, D. Phosphorus Sulfur 1987, 32, 119-144.
2. Kafarski, P.; Lejczak, B. Phosphorus, Sulfur Silicon Relat. Elem. 1991, 63, 193-215.
3. Kukhar', V. P.; Svistunova, N. Y.; Solodenko, V. A.; Soloshonok, V. A. Russ. Chem. Rev. 1993, 62, 261-278.
4. Hirschmann, R.; Smith, A. B.; Taylor, C. M.; Benkovic, P. A.; Taylor, S. D.; Yager, K. M.; Sprengeler, P. A.; Benkovic, S. J. Science 1994, 265, 234-237.
5. Bartlett, P. A.; McLaren, K. Phosphorus Sulfur 1987, 33, 1-44.
6. Jacquier, R.; Quazzani, F.; Roumestant, M.-L.; Viallefont, P. Phosphorus Sulfur 1988, 36, 73-77.
7. Sawamura, M.; Ito, Y.; Hayashi, T. Tetrahedron Lett. 1989, 30, 2247-2250.
8. Hanessian, S.; Bennani, Y. L.; Delorme, D. Tetrahedron Lett. 1990, 31, 6461-6464.
9. Shaun Murphree, S.; Muller, C. L.; Padwa, A. Tetrahedron Lett. 1990, 31, 6145-6148.
10. Moberg, C.; Rakos, L.; Tottie, L. Tetrahedron Lett. 1992, 33, 2191-2194.
11. Yokomatsu, T.; Shibuya, S. Tetrahedron: Asymmetry 1992, 3, 377-378.
12. Ktmz, H. Synthesis 1992, 90-93.
13. Benmmi, Y. L.; Hanessinn, S.; Herve, Y. Synlett 1993, 35-38.
14. Shatzmiller, S.; lqeidlein, R.; Weik, C. Liebigs Ann. Chem. 1993, 955-958.
15. Bongini, A.; Camerini, R.; Hofman, S.; Panunzio, M. Tetrahedron Lett. 1994, 35, 8045-8048.
16. Noyori, R.; Tokunaga, M.; Kitamura, M. Bull. Chem. Soc. Jpn. 1995, 68, 36-56.
17. Ward, R. S. Tetrahedron: Asymmetry 1995, 6, 1475-1490.
18. Ratovelomanana-Vidal, V.; Genêt, J.-P. Can. J. Chem. 2000, 78, 846-852.
19. Faber, K. Chem.-Eur. J. 2001, 7, 5005-5010.
20. Pellissier, H. Tetrahedron 2003, 59, 8291-8327.
21. Noyori, R.; Ikeda, T.; Ohkuma, T.; Widhalm, M.; Kitamura, M.; Takaya, H.; Akutagawa, S.; Sayo, N.; Saito, T.; Taketomi, T.; Kumobayashi, H. J. Am. Chem. Soc. 1989, 111, 9134-9135.
22. Genêt, J.-P.; Pinel, C.; Mallart, S.; Juge, S.; Thorimbert, S.; Laffitte, J. A. Tetrahedron: Asymmetry 1991, 2, 555-567.
23. Mashima, K.; Matsumura, Y.; Kusano, K.; Kumobayashi, H.; Sayo, N.; Hori, Y.; Ishizaki, T.; Akutagawa, S.; Takaya, H. Chem Commun. 1991, 609-610.
24. Coulon, E.; Andrade, M. C. C. d.; Ratovelomanana-Vidal, V.; Genêt, J.-P. Tetrahedron Lett. 1998, 39, 6467-6470.
25. Makino, K.; Hiroki, Y.; Hamada, Y. J. Am. Chem. Soc. 2005, 127, 5784-5785.
26. Makino, K.; Iwasaki, M.; Hamada, Y. Org. Lett. 2006, 8, 4573-4576.
27. Lei, A.; Wu, S.; He, M.; Zhang, X. J. Am. Chem. Soc. 2004, 126, 1626-1627.
28. Mordant, C.; Dunkelmann, P.; Ratovelomanana-Vidal, V.; Genêt, J.-P. Chem. Commun. 2004, 1296-1297.
29. Makino, K.; Goto, T.; Hiroli, Y.; Hamada., Y. Angew. Chem., Int. Ed. 2004, 43, 882-884.
30. Mordant, C.; Dunkelmann, P.; Ratovelomanana-Vidal, V.; Genêt., J.-P. Eur. J. Org. Chem. 2004, 3017-3026.
31. Makino, K.; Goto, T.; Hiroki, Y.; Hamada, Y. Tetrahedron: Asymmetry 2008, 19, 2816-2828.
32. Kitamura, M.; Tokunaga, M.; Pham, T.; Lubell, W. D.; Noyori, R. Tetrahedron Lett. 1995, 36, 5769-5772.
33. Sun, Y.; Wan, X.; Guo, M.; Wang, D.; Dong, X.; Pan, Y.; Zhang, Z. Tetrahedron: Asymmetry 2004, 15, 2185-2188.
34. Sun, Y.; Wan, X.; Wang, J.; Meng, Q.; Zhang, H.; Jiang, L.; Zhang, Z. Org. Lett. 2005, 7, 5425-5427.
35. Wan, X.; Meng, Q.; Zhang, H.; Sun, Y.; Fan, W.; Zhang, Z. Org. Lett. 2007, 9, 5613-5616.
36. Sun, X.; Zhou, L.; Li, W.; Zhang, X. J. Org. Chem. 2008, 73, 1143-1146.
37. Meng, Q.; Sun, Y.; Ratovelomanana-Vidal, V.; Genêt, J. P.; Zhang, Z. J. Org. Chem. 2008, 73, 3842-3847; .
38. Li, W.; Ma, X.; Fan, W.; Tao, X.; Li, X.; Xie, X.; Zhang, Z. Org. Lett. 2011, 13, 3876-3879.
39. Fan, W.; Li, W.; Ma, X.; Tao, X.; Li, X.; Yao, Y.; Xie, X.; Zhang, Z. Chem. Commun. 2012, 48, 4247-4249.
40. Ma, X.; Li, W.; Li, X.; Tao, X.; Fan, W.; Xie, X.; Ayad, T.; Ratovelomanana-Vidal, V.; Zhang, Z. Chem. Commun. 2012, 48, 5352-5354.
41. Zhang, Z.; Qian, H.; Longmire, J.; Zhang, X. J. Org. Chem. 2000, 65, 6223-6226.
42. Saito, T.; Yokozawa, T.; Ishizaki, T.; Moroi, T.; Sayo, N.; Miura, T.; Kumobayashi, H. Adv. Synth. Catal. 2001, 343, 264-267.
43. Wu, S.; Wang, W.; Tang, W.; Lin, M.; Zhang, X. Org. Lett. 2002, 4, 4495-4497.
44. Kakei, H.; Nemoto, T.; Ohshima, T.; Shibasaki, M. Angew. Chem., Int. Ed. 2004, 43, 317-320.
45. Tsutsumi, K.; Katayama, T.; Utsumi, N.; Murata, K.; Arai, N.; Kurono, N.; Ohkuma, T. Org. Process Res. Dev. 2009, 13, 625-628.
46. Togni, A. Angew. Chem., Int. Ed. 1996, 35, 1475-1477.
47. Vogl, E. M.; Gröger, H.; Shibasaki, M. Angew. Chem., Int. Ed. 1999, 38, 1570-1577.
48. Xiao, D.; Zhang, X. Angew. Chem., Int. Ed. 2001, 40, 3425-3428.
49. Chi, Y.; Zhou, Y. G.; Zhang, X. J. Org. Chem. 2003, 68, 4120-4122.
50. Moessner, C.; Bolm, C. Angew. Chem., Int. Ed. 2005, 44, 7564-7567.
51. Legault, C. Y.; Charette, A. B. J. Am. Chem. Soc. 2005, 127, 8966-8967.
52. Hou, G.-H.; Xie, J.-H.; Wang, L.-X.; Zhou, Q.-L. J. Am. Chem. Soc. 2006, 128, 11774-11775.
53. Akiyama, T. Chem. Rev. 2007, 107, 5744-5758.
54. Zhou, Y.-G. Acc. Chem. Res. 2007, 40, 1357-1366.
55. Gemal, A. L.; Luche, J. L. J. Am. Chem. Soc. 1981, 103, 5454-5459.
56. Casy, A. F.; Drake, A. F.; Ganellin, C. R.; Mercer, A. D.; Upton, C. Chirality 1992, 4, 356-366.
57. Kolodiazhnyi, O. I. Tetrahedron: Asymmetry 2005, 16, 3295-3340.