Stereocartography: A computational mapping technique that can locate regions of maximum stereoinduction around chiral catalysts

Journal of the American Chemical Society

Volumn 124, Issue 47, 2002, Pages 14255-14267

  Lipkowitz, Kenny B ^a   D'Hue, Cedric A ^a   Sakamoto, Taka ^a   Stack, Jonathan N ^a  

^a INDIANA UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

COMPUTATIONAL METHODS; MAPPING;

DIELS-ALDER REACTIONS; STEREOCARTOGRAPHY;

CATALYSTS;

ARTICLE; CATALYST; CHIRALITY; DIELS ALDER REACTION; ENERGY; MATHEMATICAL COMPUTING; MOLECULAR MODEL; STEREOCHEMISTRY; TECHNIQUE;

EID: 0037184415     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0207192     Document Type: Article

References (45)

1. (a) Stinson, S. C. Chem. Eng. News 2001, 79-97.
2. (b) Stinson, S. C. Chem. Eng. News 1995, 44-74.
3. (c) Stinson, S. C. Chem. Eng. News 1994, 38-72.
4. (d) Stinson, S. C. Chem. Eng. News 1993, 38-65.
5. Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag: New York, 1999; 3-vols.; ISBN 3-540-64336-2.
6. Kanemasa, S.; Oderaotashi, Y.; Yamamoto, H.; Tanaka, J.; Wada, E.; Curran, D. P. J. Org. Chem. 1997, 62, 6454-6455.
7. Cambridge Structural Database: Available from Wavefunction, Inc., 18401 Von Karman, Suite 370, Irvine, CA 92715.
8. Spartan: Available from Wavefunction, Inc., 18401 Von Karman, Suite 370, Irvine, CA 92715.
9. Mohamadi, F.; Richards, N. G. J.; Guida, W. C.; Liskamp, R.; Lipton, M.; Caufield, C.; Chang, G.; Hendrickson, T.; Still, W. C. J. Comput. Chem. 1990, 11, 440-467.
10. 6 To maximize usage of existing and remote machines, pvm_grid is parallelized using the PVM (Parallel Virtual Machine) Library (http://www.epm.ornl.gov/pvm/pvm_home.html).
11. AMBER* is a modified version of the AMBER force field contained in MacroModel.
12. Numerical algorithms Group, IRIS Explorer. IRIS Explorer Center (North America), Downers Grove, IL 60551-5702 or via http://www.nag.co.uk/Welcome_IEC.html.
13. Narasaka, K.; Iwasawa, N.; Inoue, M.; Yamada, T.; Nakashima, M.; Sugimori, J. J. Am. Chem. Soc. 1989. 111, 5340-5345.
14. Seebach, D.; Plattner, D. A.; Beck, A. K.; Wang, Y. M.; Hunziker, D.; Petter, W. Helv. Chem. Acta 1992, 75, 2171-2192.
15. Kanemasa, S.; Oderatoshi, Y.; Yamamoto, H.; Tanaka, J.; Wada, E. J. Org. Chem. 1997, 62, 6454-6455.
16. Kanemasa, S.; Oderaotoshi, Y.; Sakaguchi, S.; Yamamoto, H.; Tanaka, J.; Wada, E.; Curran, D. P. J. Am. Chem. Soc. 1998, 120, 3074-3088.
17. Ghosh, A. K.; Matsuda, H. Org. Lett. 1999, 1, 2157-2159.
18. Corey, E. J.; Imwinkelried, R.; Pikul, S.; Xiang, Y. B. J. Am. Chem. Soc. 1989, 111, 5493-5495.
19. Corey, E. J.; Sashar, S. J. Am. Chem. Soc. 1992, 114, 7938-7939.
20. (a) Evans, D. A.; Woerpel, K. A.; Hinman, M. M.; Faul, M. M. J. Am. Chem. Soc. 1991, 113, 726-728.
21. (b) Lowenthal, R. E.; Abiko, A.; Masamune, S. Tetrahedron Lett. 1990, 31, 6005-6008.
22. (c) Müller, D.; Umbricht, B. W.; Pfaltz, A. Helv. Chim. Acta 1991, 74, 232-240.
23. (d) Evans, D. A.; Faul, M. M.; Bilodeau, M. T.; Anderson, B. A.; Barnes, D. M. J. Am. Chem. Soc. 1993, 115, 726-728.
24. (e) Evans, D. A.; Faul, M. M.; Bilodeau, M. T. J. Am. Chem. Soc. 1994, 116, 2742-2753.
25. Evans, D. A.; Miller, S. J.; Lectka, T.; von Matt, P. J. Am. Chem. Soc. 1999, 121, 7559-7573.
26. Helmchen, G.; Sagasser, I. Tetrahedron Lett. 1998, 39, 261-264.
27. (a) Evans, D. A.; Miller, S. J.; Lectka, T. J. Am. Chem. Soc. 1993, 115, 6460-6461.
28. (b) Evans, D. A.; Lectka, T.; Miller, S. J. Tetrahedron Lett. 1993, 34, 7027-7030.
29. (c) Dias, L. C. J. Braz. Chem. Soc. 1997, 8 (4), 289-332.
30. (d) Hoveyda, A. H.; Morken, J. P. Angew. Chem., Int. Ed. Engl. 1996, 35, 1262-1284.
31. Hori, K.; Watanabe, K.; Abe, I.; Michiko, K. Tetrahedron Lett. 2001, 42, 7617-7619.
32. Takacs, J. M.; Quincy, D. A.; Shay, W.; Jones, B. E.; Ross, C. R.; Tetrahedron: Asymmetry 1997, 8, 3079-3087.
33. Asano, H.; Katayama, K.; Kurosawa, H. Inorg. Chem. 1996, 35, 5760-5761.
34. Davies, D. L.; Fawcett, J.; Garratt, S. A.; Russell, D. R. J. Chem. Soc., Chem. Commun. 1997, 1351-1352.
35. Kündig, E. P.; Bourdin, B.; Bernardinelli, G. Angew. Chem., Int. Ed. Engl. 1994, 33, 1856-1858.
36. Yamamoto, H.; Pfaltz, A.; Jacobsen, E. N. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, 1999; Vol. 3, pp 1181-1182.
37. Evans, D. A.; Murry, J. A.; von Matt, P.; Norcross, R. D.; Miller, S. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 798-800.
38. Rebierre, F.; Riant, O.; Kagan, H. B. Tetrahedron: Asymmetry 1990, 3, 199-214.
39. Hashimoto, S.; Komeshima N.; Koga, K. J. Chem. Soc., Chem. Commun. 1979, 437-438.
40. Hawkins, J. M.; Loren, S. J. Am. Chem. Soc. 1991, 113, 7794-7795.
41. Maruoka, K.; Concepcion, A. B.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1992, 65, 3501-3503.
42. Holz, J.; Stürmer, R.; Schmidt, H.-J.; Heller, D.; Krimmer, H.-P.; Börner, A. Eur. J. Org. Chem. 2001, 4615-4624.
43. (a) Cha, A. E. Washington Post, Feb 21, 2002, p E06.
44. (b) See the website on In-Silico Screening for Anthrax Toxin Inhibitors: http://www.chem.ox.ac.uk/anthrax/.
45. (c) For more about high throughput computing using collections of distributively owned computing resources see, e.g., Condor website: http://www.cs.wisc.edu/condor.