Theoretical study of the mechanism of Hantzsch ester hydrogenation of imines catalyzed by chiral BINOL-phosphoric acids

Journal of the American Chemical Society

Volumn 130, Issue 27, 2008, Pages 8741-8747

  Simón, Luis ^a   Goodman, Jonathan M ^a  

^a UNILEVER RESEARCH   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ACIDS; ENANTIOSELECTIVITY; ESTERIFICATION; ESTERS; HYDROGENATION; LEAD; MECHANISMS; NITROGEN COMPOUNDS; PHOSPHORIC ACID;

AMERICAN CHEMICAL SOCIETY (ACS); DFT METHODS; ESTER HYDROGENATION;

ORGANIC COMPOUNDS;

2,2' DIHYDROXY 1,1' BINAPHTHYL; BRONSTED ACID; ESTER DERIVATIVE; IMINE; PHOSPHORIC ACID DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL INTERACTION; CHIRALITY; DENSITY FUNCTIONAL THEORY; ENANTIOSELECTIVITY; HYDROGENATION; REACTION ANALYSIS; THEORETICAL STUDY;

EID: 46949083787     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja800793t     Document Type: Article

References (60)

1. Rueping, M.; Azap, C.; Sugiono, E.; Theissmann, T. Synlett 2005, 2367-2369.
2. Rueping, M.; Theissmann, T.; Antonchick, A. P. Synlett 2006, 1071-1074.
3. Itoh, T.; Nagata, K.; Miyazaki, M.; Ishikawa, H.; Kurihara, A.; Ohsawa, A. Tetrahedron 2004, 60, 6649-6655.
4. Connon, S. J. Org. Biomed. Chem. 2007, 5, 3407-3417.
5. You, S.-L. Chem. - Asian J. 2007, 2, 820-827.
6. Akiyama, T. Chem. Rev. 2007, 107, 5744-5758.
7. Rueping, M.; Sugiono, E.; Azap, C.; Theissmann, T.; Bolte, M. Org. Lett. 2005, 7, 3781-3783.
8. Hoffmann, S.; Nicoletti, M.; List, B. J. Am. Chem. Soc. 2006, 128, 13074-13075.
9. Rueping, M.; Antonchick, A. P.; Theissmann, T. Angew. Chem., Int. Ed. 2006, 45, 3683-3686.
10. Rueping, M.; Antonchick, A. P.; Theissmann, T. Angew. Chem., Int. Ed. 2006, 45, 6751-6755.
11. Storer, R. I.; Carrera, D. E.; Ni, Y.; MacMillan, D. W. C. J. Am. Chem. Soc. 2006, 128, 84-86.
12. Yang, J. W.; List, B. Org. Lett. 2006, 8, 5653-5655.
13. Li, G.; Liang, Y.; Antilla, J. C. J. Am. Chem. Soc. 2007, 129, 5830-5831.
14. Zhou, J.; List, B. J. Am. Chem. Soc. 2007, 129, 7498-7499.
15. Hoffmann, S.; Seayad, A. M.; List, B. Angew. Chem., Int. Ed. 2005, 44, 7424-7427.
16. Rueping, M.; Antonchick, A. P. Angew. Chem., Int. Ed. 2007, 46, 4562-4565.
17. Guo, Q.-S.; Du, D.-M.; Xu, J. Angew. Chem., Int. Ed. 2008, 47, 759-762.
18. Rueping, M.; Sugiono, E.; Azap, C. Angew. Chem., Int. Ed. 2006, 45, 2617-2619.
19. Rueping, M.; Sugiono, E.; Moreth, S. A. Adv. Synth. Catal. 2007, 349, 759-764.
20. Yamanaka, M.; Itoh, J.; Fuchibe, K.; Akiyama, T. J. Am. Chem. Soc. 2007, 129, 6756-6764.
21. Guo, Q.-X.; Liu, H.; Guo, C.; Luo, S.-W.; Gu, Y.; Gong, L.-Z. J. Am. Chem. Soc. 2007, 129, 3790-3791.
22. Uraguchi, D.; Terada, M. J. Am. Chem. Soc. 2004, 126, 5356-5357.
23. Akiyama, T.; Itoh, J.; Yokota, K.; Fuchibe, K. Angew. Chem., Int. Ed. 2004, 43, 1566-1568.
24. Liu, H.; Cun, L.-F.; Mi, A.-Q.; Jiang, Y.-Z.; Gong, L.-Z. Org. Lett. 2006, 8, 6023-6026.
25. Qiang Kang, Q.; Zhao, Z.-A.; You, S.-L. J. Am. Chem. Soc. 2007, 129, 1484-1485.
26. Jia, Y.-X.; Zhong, J.; Zhu, S.-F.; Zhang, C.-M.; Zhou, Q.-L. Angew. Chem., Int. Ed. 2007, 46, 5565-5567.
27. Li, G.; Rowland, G. B.; Rowland, E. B.; Antilla, J. C. Org. Lett. 2007, 9, 4065-4068.
28. Terada, M.; Sorimachi, K. J. Am. Chem. Soc. 2007, 129, 292-293.
29. Terada, M.; Yokoyama, S.; Sorimachi, K.; Uraguchi, D. Adv. Synth. Catal. 2007, 349, 1863-1867.
30. Terada, M.; Machioka, K.; Sorimachi, K. Angew. Chem., Int. Ed. 2006, 45, 2254-2257.
31. Terada, M.; Machioka, K.; Sorimachi, K. J. Am. Chem. Soc. 2007, 129, 10336-10337.
32. Pan, S. C.; Zhou, J.; List, B. Angew. Chem., Int. Ed. 2007, 46, 612-614.
33. Jiang, J.; Yu, J.; Sun, X.-X.; Rao, Q.-Q.; Gong, L.-Z. Angew. Chem., Int. Ed. 2008, 47, 2458-2462.
34. Wanner, M. J.; van der Haas, R. N. S.; de Cuba, K. R.; van Maarseveen, J. H.; Hiemstra, H. Angew. Chem., Int. Ed. 2007, 46, 7485-7487.
35. Akiyama, T.; Monta, H.; Itoh, J.; Fuchibe, K. Org. Lett. 2005, 7, 2583-2585.
36. Rueping, M.; Ieawsuwan, W.; Antonchick, A. P.; Nachtsheim, B. J. Angew. Chem., Int. Ed. 2007, 46, 2097-2100.
37. Easson, L. H.; Stedman, E. J. Biochem. 1933, 27, 1257-1266.
38. Jaguar, version 6.5; Schrödinger Inc.: New York, NY, 2006.
39. Becke, A. D. J. Chem. Phys. 1983, 98, 5648-5652.
40. Gill, P. M. W.; Johnson, B. G.; Pople, J. A.; Frisch, M. J. J. Chem. Phys. 1992, 197, 499-505.
41. Krishnam, R.; Binkley, J. S.; Seeger, R.; Pople, J. A. J. Chem. Phys. 1980, 72, 650-654.
42. Clark, T.; Chandrasekhar, J.; Schleyer, P. v. R. J. Comput. Chem. 1983, 4, 294-301.
43. Glendening, E. D.; Weinhold, F. J. Comput. Chem. 1998, 19, 593-609.
44. Dapprich, S.; Komaromi, I.; Byun, K. S.; Morokuma, K.; Frisch, M. J. J. Mol. Struct. (THEOCHEM) 1999, 461-462.
45. Svensson, M.; Humbel, S.; Morokuma, K. J. Chem. Phys. 1996, 105, 3654-3661.
46. Vreven, T.; Morokuma, K. J. Comput. Chem. 2000, 21, 1419-1432.
47. Frisch, M. J.; Gaussian 03, revision D.03; Gaussian, Inc.: Wallingford CT, 2004.
48. Dewar, M. J. S.; Reynolds, C. H. J. Comput. Chem. 1986, 2, 140-143.
49. Stewart, J. J. P. J. Comput. Chem. 1989, 10, 221-264.
50. Cornell, W. D.; Cieplak, P.; Bayly, C. I.; Gould, I. R., Jr.; Ferguson, D. M.; Spellmeyer, D. C.; Fox, T.; Caldwell, J. W.; Kollman, P. A. J. Am. Chem. Soc. 1995, 117, 5179-5179.
51. Mayo, S. L.; Olafson, B. D.; Goddard, W. A., III. J. Phys. Chem. 1990, 94, 8897-8909.
52. Rappé, A. K.; Casewit, C. J.; Colwell, K. S.; Goddard, W. A., III.; Skid, W. M. J. Am. Chem. Soc. 1992, 114, 10024-10035.
53. Zhao, Y.; Truhlar, D. G. J. Chem. Theory Comput. 2005, 7, 415-432.
54. Cammi, R.; Mennucci, B.; Tomasi, J. J. Phys. Chem. A 2000, 104, 5631-5637.
55. Cammi, R.; Mennucci, B.; Tomasi, J. J. Phys. Chem. A 1999, 103, 9100-9108.
56. Cossi, M.; Rega, N.; Scalmani, M.; Barone, V. J. Chem. Phys. 2001, 114, 5691-5701.
57. Cossi, M.; Scalmani, G.; Rega, N.; Barone, V. J. Chem. Phys. 2002, 117, 43-54.
58. Cossi, M.; Scalmani, G.; Rega, N.; Barone, V. J. Comput. Chem. 2003, 24, 669-681.
59. Barone, V.; Cossi, M.; Tomassi, J. J. Chem. Phys. 1997, 107, 3210-3221.
60. Vachal, P.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 10012-10014.