Transition state modeling and catalyst design for hydrogen bond-stabilized enolate formation

Journal of Organic Chemistry

Volumn 70, Issue 19, 2005, Pages 7755-7760

  Zhu, Yimin ^a   Drueckhammer, Dale G ^a  

^a STONY BROOK UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINES; CATALYSTS; CONFORMATIONS; ELECTRONS; HYDROGEN BONDS; ION EXCHANGE; KETONES; METHANOL; PROTONS; SYNTHESIS (CHEMICAL);

CATALYTIC MOETIES; ENOLATES; TRANSITION STATE; TRANSITION STATE MODELING;

CATALYSIS;

ALKENE DERIVATIVE; AMINE; ENOLATE; OXYGEN; THIOUREA; UNCLASSIFIED DRUG;

ARTICLE; CALCULATION; CATALYSIS; CATALYST; CHEMICAL STRUCTURE; COMPLEX FORMATION; COMPUTER PROGRAM; CONFORMATION; DATA BASE; HYDROGEN BOND; MODEL; PROTON TRANSPORT; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 24944516202     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0513818     Document Type: Article

References (53)

1. Gröger, H.; Wilken, J. Angew. Chem., Int. Ed. 2001, 40, 529-532.
2. Horstmann, T. E.; Guerin, D. J.; Miller, S. J. Angew. Chem., Int. Ed. 2000, 39, 3635-3638.
3. French, R. R.; Holzer, P.; Leuenberger, M. G.; Woggon, W.-D. Angew. Chem., Int. Ed. 2000, 39, 1267-1269.
4. Yan, J.; Breslow, R. Tetrahedron Lett. 2000, 41, 2059-2062.
5. List, B.; Lerner, R. A.; Barbas, C. F., III. J. Am. Chem. Soc. 2000, 122, 2395-2396.
6. List, B. Acc. Chem. Res. 2004, 37, 548-557.
7. Saito, S.; Yamamoto, H. Acc. Chem. Res. 2004, 37, 570-579.
8. Notz, W.; Tanaka, F.; Barbas, C. F., III. Acc. Chem. Res. 2004, 37, 580-591.
9. Morris, A. J.; Tolan, D. R. Biochemistry 1994, 33, 12291-12297.
10. Hall, D. R.; Leonard, G. A.; Reed, C. D.; Watt, C. I.; Berry, A.; Hunter, W. N. J. Mol. Biol. 1999, 287, 383-394.
11. Kurz, L. C.; Shah, S.; Crane, B. R.; Donald, L. J.; Duckworth, H. W.; Drysdale, G. R. Biochemistry 1992, 31, 7899-7907.
12. Kluger, R. Chem. Rev. 1990, 90, 1151-1169.
13. Um, P.-J.; Drueckhammer, D. G. J. Am. Chem. Soc. 1998, 120, 5605-5610.
14. Dinh, P. M.; Williams, J. M. J.; Harris, W. Tetrahedron Lett. 1999, 40, 749-752.
15. Siegel, B.; Pinter, A.; Breslow, R. J. Am. Chem. Soc. 1977, 99, 2309-2312.
16. Breslow, R.; Graf, A. J. Am. Chem. Soc. 1993, 115, 10988-10989.
17. Deeper, J. M.; Breslow, R. J. Am. Chem. Soc. 1994, 116, 12081-12082.
18. Breslow, R.; Desper, J. M.; Huang, Y. Tetrahedron Lett. 1996, 37, 2541-2544.
19. Binder, W. H.; Menger, F. M. Tetrahedron Lett. 1996, 37, 8963-8966.
20. Fenniri, H.; Lehn, J.-M.; Marquis-Rigault, A. J. Am. Chem. Soc. 1996, 35, 337-339.
21. Wolfe, J.; Muehldorf, A.; Rebek, J. J. Am. Chem. Soc. 1991, 113, 1453-1454.
22. Snowden, T. S.; Bisson, A. P.; Anslyn, E. V. Bioorg. Med. Chem. 2001, 9, 2467-2478.
23. Chin, T.; Gao, Z.; Lelouche, I.; Shin, Y. K.; Purandare, A.; Knapp, S.; Isied, S. S. J. Am. Chem. Soc. 1997, 119, 12849-12858.
24. Kimura, E.; Kitamura, H.; Koike, T.; Shiro, M. J. Am. Chem. Soc. 1997, 119, 10909-10919.
25. Kimura, E.; Gotoh, T.; Koike, T.; Shiro, M. J. Am. Chem. Soc. 1999, 121, 1267-1274.
26. Kelly-Rowley, A. M.; Lynch, V. M.; Anslyn, E. V. J. Am. Chem. Soc. 1995, 117, 3438-3447.
27. Snowden, T. S.; Bisson, A. P.; Anslyn, E. V. J. Am. Chem. Soc. 1999, 121, 6324-6325.
28. Lauri, G.; Bartlett, P. A. J. Comput.-Aided Mol. Des. 1994, 8, 51-66.
29. (a) Bartlett, P. A.; Shea, G. T.; Telfer, S. J.; Waterman, S. In Molecular Recognition: Chemical and Biological Problems; Roberts, S. M., Ed.; Royal Society of Chemistry: London, 1989; pp 182-196.
30. (b) Bartlett, P. A.; Etzkorn, F. A.; Guo, T.; Lauri, G.; Liu, K.; Lipton, M.; Morgan, B. P.; Shea, G. T. In Chemistry at the Frontiers of Medicine, Proceedings of the Robert A. Welch Foundation Conference on Chemical Research XXXV, Houston, TX, Oct 28-29, 1991; Robert A. Welch Foundation: Houston, TX, 1991; pp 45-68.
31. Kozlowski, M. C.; Panda, M. J. Mol. Graphics Modell. 2002, 20, 399-409.
32. Yang, W.; He, H.; Drueckhammer, D. G. Angew. Chem., Int. Ed. 2002, 40, 1714-1718.
33. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Gui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, revision A.1; Gaussian, Inc.: Wallingford, CT, 2004.
34. Lucet, D.; Sabelle, S.; Kostelitz, O.; Le Gall, T.; Mioskowski, C. Eur. J. Org. Chem. 1999, 2583-2591.
35. Park, S.; Hayes, B. L.; Marankan, F.; Mulhearn, D. C.; Wanna, L.; Mesecar, A. D.; Santarsiero, B. D.; Johnson, M. E.; Venton, D. L. J. Med. Chem. 2003, 46, 936-953.
36. Novak, L.; Hanania, M.; Kovacs, P.; Kovacs, C. E.; Kolonits, P.; Szantay, C. Synth. Commun. 1999, 29, 1757-1766.
37. Pihko, P. M. Angew. Chem., Int. Ed. 2004, 43, 2062-2064.
38. Ma, D.; Cheng, K. Tetrahedron: Asymmetry 1999, 713-719.
39. Sohtome, Y.; Tanatani, A.; Hashimoto, Y.; Nagasawa, K. Tetrahedron Lett. 2004, 45, 5589-5592.
40. Joly, G. D.; Jacobsen, E. N. J. Am. Chem. Soc. 2004, 726, 4102-4103.
41. Wenzel, A. G.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 12964-12965.
42. Benning, M. M.; Taylor, K. L.; Liu, R.; Yang, G.; Xiang, H.; Wesenberg, G.; Dunaway-Mariano, D.; Holden, H. M. Biochemistry 1996, 35, 8103-8109.
43. Bahnson, B. J.; Anderson, V. E.; Petsko, G. A. Biochemistry 2002, 41, 2621-2629.
44. (a) Babbit, P. C.; Gerlt, J. A. J. Biol. Chem. 1997, 272, 30591-30594.
45. (b) Xiang, H.; Luo, L.; Taylor, K. L.; Dunaway-Mariano, D. Biochemistry 1999, 38, 7638-7652.
46. Kim, J. J.; Wang, M.; Paschke, R. Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 7523-7527.
47. Djordjevic, S.; Pace, C. P.; Stankovich, M. T.; Kim, J. J. Biochemistry 1995, 34, 2163-2171.
48. (a) Usher, K. C.; Remington, S. J.; Martin, D. P.; Drueckhammer, D. G. Biochemistry 1994, 33, 7753-7759.
49. (b) Yang, W.; Drueckhammer, D. G. J. Phys. Chem. B 2003, 107, 5986-5994.
50. Dinovo, E. C.; Boyer, P. D. J. Biol. Chem. 1971, 246, 4586-4593.
51. Zhong, Z.; Snowden, T. S.; Best, M. D.; Anslyn, E. V. J. Am. Chem. Soc. 2004, 126, 3488-3495.
52. Bernasconi, C. F. Acc. Chem. Res. 1992, 25, 9-16.
53. Bach, R. D.; Thorpe, C.; Dmitrenko, O. J. Phys. Chem. B 2002, 106, 4325-4335.