Recognition-mediated facilitation of a disfavored Diels - Alder reaction

Organic Letters

Volumn 1, Issue 7, 1999, Pages 1087-1090

  Bennes, Raphaël ^a   Philp, Douglas ^a   Spencer, Neil ^a   Kariuki, Benson M ^a   Harris, Kenneth D M ^a  

^a UNIVERSITY OF BIRMINGHAM   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000011153     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol9908880     Document Type: Article

References (44)

1. Ichihara, A.; Oikawa, H. Curr. Org. Chem. 1998, 2, 365. Katayama, K.; Kobayashi, T.; Oikawa, H.; Honma, M.; Ichihara, A. Biochim. Biophys. Acta 1998, 1384, 387. Catalytic antibodies have been described which are capable of catalyzing cycloaddition reactions. Hilvert, D.; Hill, K. W.; Nared, K. D.; Auditor, M.-T. M. J. Am. Chem. Soc. 1989, 111, 9261. Braisted, A. C.; Schultz, P, G. J. Am. Chem. Soc. 1990, 112, 7430, Gouverneur, V. E.; Houk, K. N.; de Pascual-Theresa, B.; Beno, B.; Janda, K. D.; Lerner, R. A. Science 1993, 262, 204. Romesberg, F. E.; Spiller, B.; Schultz, P.; Stevens, R. C. Science 1998, 279, 1929. Heine, A.; Stura, E. A.; Yli-Kauhaluoma, J. T.; Gao, C.; Deng, Q.; Beno, B. R.; Houk, K. N.; Janda, K. D.; Wilson, I. A. Science 1998, 279, 1935.
2. Ichihara, A.; Oikawa, H. Curr. Org. Chem. 1998, 2, 365. Katayama, K.; Kobayashi, T.; Oikawa, H.; Honma, M.; Ichihara, A. Biochim. Biophys. Acta 1998, 1384, 387. Catalytic antibodies have been described which are capable of catalyzing cycloaddition reactions. Hilvert, D.; Hill, K. W.; Nared, K. D.; Auditor, M.-T. M. J. Am. Chem. Soc. 1989, 111, 9261. Braisted, A. C.; Schultz, P, G. J. Am. Chem. Soc. 1990, 112, 7430, Gouverneur, V. E.; Houk, K. N.; de Pascual-Theresa, B.; Beno, B.; Janda, K. D.; Lerner, R. A. Science 1993, 262, 204. Romesberg, F. E.; Spiller, B.; Schultz, P.; Stevens, R. C. Science 1998, 279, 1929. Heine, A.; Stura, E. A.; Yli-Kauhaluoma, J. T.; Gao, C.; Deng, Q.; Beno, B. R.; Houk, K. N.; Janda, K. D.; Wilson, I. A. Science 1998, 279, 1935.
3. Ichihara, A.; Oikawa, H. Curr. Org. Chem. 1998, 2, 365. Katayama, K.; Kobayashi, T.; Oikawa, H.; Honma, M.; Ichihara, A. Biochim. Biophys. Acta 1998, 1384, 387. Catalytic antibodies have been described which are capable of catalyzing cycloaddition reactions. Hilvert, D.; Hill, K. W.; Nared, K. D.; Auditor, M.-T. M. J. Am. Chem. Soc. 1989, 111, 9261. Braisted, A. C.; Schultz, P, G. J. Am. Chem. Soc. 1990, 112, 7430, Gouverneur, V. E.; Houk, K. N.; de Pascual-Theresa, B.; Beno, B.; Janda, K. D.; Lerner, R. A. Science 1993, 262, 204. Romesberg, F. E.; Spiller, B.; Schultz, P.; Stevens, R. C. Science 1998, 279, 1929. Heine, A.; Stura, E. A.; Yli-Kauhaluoma, J. T.; Gao, C.; Deng, Q.; Beno, B. R.; Houk, K. N.; Janda, K. D.; Wilson, I. A. Science 1998, 279, 1935.
4. Ichihara, A.; Oikawa, H. Curr. Org. Chem. 1998, 2, 365. Katayama, K.; Kobayashi, T.; Oikawa, H.; Honma, M.; Ichihara, A. Biochim. Biophys. Acta 1998, 1384, 387. Catalytic antibodies have been described which are capable of catalyzing cycloaddition reactions. Hilvert, D.; Hill, K. W.; Nared, K. D.; Auditor, M.-T. M. J. Am. Chem. Soc. 1989, 111, 9261. Braisted, A. C.; Schultz, P, G. J. Am. Chem. Soc. 1990, 112, 7430, Gouverneur, V. E.; Houk, K. N.; de Pascual-Theresa, B.; Beno, B.; Janda, K. D.; Lerner, R. A. Science 1993, 262, 204. Romesberg, F. E.; Spiller, B.; Schultz, P.; Stevens, R. C. Science 1998, 279, 1929. Heine, A.; Stura, E. A.; Yli-Kauhaluoma, J. T.; Gao, C.; Deng, Q.; Beno, B. R.; Houk, K. N.; Janda, K. D.; Wilson, I. A. Science 1998, 279, 1935.
5. Ichihara, A.; Oikawa, H. Curr. Org. Chem. 1998, 2, 365. Katayama, K.; Kobayashi, T.; Oikawa, H.; Honma, M.; Ichihara, A. Biochim. Biophys. Acta 1998, 1384, 387. Catalytic antibodies have been described which are capable of catalyzing cycloaddition reactions. Hilvert, D.; Hill, K. W.; Nared, K. D.; Auditor, M.-T. M. J. Am. Chem. Soc. 1989, 111, 9261. Braisted, A. C.; Schultz, P, G. J. Am. Chem. Soc. 1990, 112, 7430, Gouverneur, V. E.; Houk, K. N.; de Pascual-Theresa, B.; Beno, B.; Janda, K. D.; Lerner, R. A. Science 1993, 262, 204. Romesberg, F. E.; Spiller, B.; Schultz, P.; Stevens, R. C. Science 1998, 279, 1929. Heine, A.; Stura, E. A.; Yli-Kauhaluoma, J. T.; Gao, C.; Deng, Q.; Beno, B. R.; Houk, K. N.; Janda, K. D.; Wilson, I. A. Science 1998, 279, 1935.
6. Ichihara, A.; Oikawa, H. Curr. Org. Chem. 1998, 2, 365. Katayama, K.; Kobayashi, T.; Oikawa, H.; Honma, M.; Ichihara, A. Biochim. Biophys. Acta 1998, 1384, 387. Catalytic antibodies have been described which are capable of catalyzing cycloaddition reactions. Hilvert, D.; Hill, K. W.; Nared, K. D.; Auditor, M.-T. M. J. Am. Chem. Soc. 1989, 111, 9261. Braisted, A. C.; Schultz, P, G. J. Am. Chem. Soc. 1990, 112, 7430, Gouverneur, V. E.; Houk, K. N.; de Pascual-Theresa, B.; Beno, B.; Janda, K. D.; Lerner, R. A. Science 1993, 262, 204. Romesberg, F. E.; Spiller, B.; Schultz, P.; Stevens, R. C. Science 1998, 279, 1929. Heine, A.; Stura, E. A.; Yli-Kauhaluoma, J. T.; Gao, C.; Deng, Q.; Beno, B. R.; Houk, K. N.; Janda, K. D.; Wilson, I. A. Science 1998, 279, 1935.
7. Ichihara, A.; Oikawa, H. Curr. Org. Chem. 1998, 2, 365. Katayama, K.; Kobayashi, T.; Oikawa, H.; Honma, M.; Ichihara, A. Biochim. Biophys. Acta 1998, 1384, 387. Catalytic antibodies have been described which are capable of catalyzing cycloaddition reactions. Hilvert, D.; Hill, K. W.; Nared, K. D.; Auditor, M.-T. M. J. Am. Chem. Soc. 1989, 111, 9261. Braisted, A. C.; Schultz, P, G. J. Am. Chem. Soc. 1990, 112, 7430, Gouverneur, V. E.; Houk, K. N.; de Pascual-Theresa, B.; Beno, B.; Janda, K. D.; Lerner, R. A. Science 1993, 262, 204. Romesberg, F. E.; Spiller, B.; Schultz, P.; Stevens, R. C. Science 1998, 279, 1929. Heine, A.; Stura, E. A.; Yli-Kauhaluoma, J. T.; Gao, C.; Deng, Q.; Beno, B. R.; Houk, K. N.; Janda, K. D.; Wilson, I. A. Science 1998, 279, 1935.
8. For a review of the use of furan Diels-Alder chemistry in synthesis, see: Kappe, C. O.; Murphree, S. S.; Padwa, A. Tetrahedron 1997, 53, 14179. For reviews of intramolecular Diels-Alder reactions, see: Brieger, G.; Bennett, J. N. Chem. Rev. 1980, 80, 63. Fallis, A. G. Can. J. Chem. 1984, 62, 183. Ciganek, E. Org. React. 1984, 32, 1. Craig, D. Chem. Soc. Rev. 1987, 16, 187. Fallis, A. G. Acc. Chem. Res. 1999, 32, 464.
9. For a review of the use of furan Diels-Alder chemistry in synthesis, see: Kappe, C. O.; Murphree, S. S.; Padwa, A. Tetrahedron 1997, 53, 14179. For reviews of intramolecular Diels-Alder reactions, see: Brieger, G.; Bennett, J. N. Chem. Rev. 1980, 80, 63. Fallis, A. G. Can. J. Chem. 1984, 62, 183. Ciganek, E. Org. React. 1984, 32, 1. Craig, D. Chem. Soc. Rev. 1987, 16, 187. Fallis, A. G. Acc. Chem. Res. 1999, 32, 464.
10. For a review of the use of furan Diels-Alder chemistry in synthesis, see: Kappe, C. O.; Murphree, S. S.; Padwa, A. Tetrahedron 1997, 53, 14179. For reviews of intramolecular Diels-Alder reactions, see: Brieger, G.; Bennett, J. N. Chem. Rev. 1980, 80, 63. Fallis, A. G. Can. J. Chem. 1984, 62, 183. Ciganek, E. Org. React. 1984, 32, 1. Craig, D. Chem. Soc. Rev. 1987, 16, 187. Fallis, A. G. Acc. Chem. Res. 1999, 32, 464.
11. For a review of the use of furan Diels-Alder chemistry in synthesis, see: Kappe, C. O.; Murphree, S. S.; Padwa, A. Tetrahedron 1997, 53, 14179. For reviews of intramolecular Diels-Alder reactions, see: Brieger, G.; Bennett, J. N. Chem. Rev. 1980, 80, 63. Fallis, A. G. Can. J. Chem. 1984, 62, 183. Ciganek, E. Org. React. 1984, 32, 1. Craig, D. Chem. Soc. Rev. 1987, 16, 187. Fallis, A. G. Acc. Chem. Res. 1999, 32, 464.
12. For a review of the use of furan Diels-Alder chemistry in synthesis, see: Kappe, C. O.; Murphree, S. S.; Padwa, A. Tetrahedron 1997, 53, 14179. For reviews of intramolecular Diels-Alder reactions, see: Brieger, G.; Bennett, J. N. Chem. Rev. 1980, 80, 63. Fallis, A. G. Can. J. Chem. 1984, 62, 183. Ciganek, E. Org. React. 1984, 32, 1. Craig, D. Chem. Soc. Rev. 1987, 16, 187. Fallis, A. G. Acc. Chem. Res. 1999, 32, 464.
13. For a review of the use of furan Diels-Alder chemistry in synthesis, see: Kappe, C. O.; Murphree, S. S.; Padwa, A. Tetrahedron 1997, 53, 14179. For reviews of intramolecular Diels-Alder reactions, see: Brieger, G.; Bennett, J. N. Chem. Rev. 1980, 80, 63. Fallis, A. G. Can. J. Chem. 1984, 62, 183. Ciganek, E. Org. React. 1984, 32, 1. Craig, D. Chem. Soc. Rev. 1987, 16, 187. Fallis, A. G. Acc. Chem. Res. 1999, 32, 464.
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20. Kang, J.; Hilmersson, G.; Santamaria, J.; Rebek, J., Jr. J. Am. Chem. Soc. 1998, 120, 7389. Kang, J.; Hilmersson, G.; Santamaria, J.; Rebek, J., Jr. J. Am. Chem. Soc. 1998, 120, 3650. Marty, M.; Clyde-Watson, Z.; Twyman, L. J.; Nakash, M.; Sanders, J. K. M. Chem. Commun. 1998, 2265. Hamilton, A. D.; Hirst, S. C. J. Am. Chem. Soc. 1991, 113, 382. Tripathy, R.; Carroll, P. J.; Thornton, E. R. J. Am. Chem. Soc. 1991, 113, 7630. Kelly, T. R.; Ekkundi, V. S.; Meghani, P. Tetrahedron Lett. 1990, 31, 3381.
21. Kang, J.; Hilmersson, G.; Santamaria, J.; Rebek, J., Jr. J. Am. Chem. Soc. 1998, 120, 7389. Kang, J.; Hilmersson, G.; Santamaria, J.; Rebek, J., Jr. J. Am. Chem. Soc. 1998, 120, 3650. Marty, M.; Clyde-Watson, Z.; Twyman, L. J.; Nakash, M.; Sanders, J. K. M. Chem. Commun. 1998, 2265. Hamilton, A. D.; Hirst, S. C. J. Am. Chem. Soc. 1991, 113, 382. Tripathy, R.; Carroll, P. J.; Thornton, E. R. J. Am. Chem. Soc. 1991, 113, 7630. Kelly, T. R.; Ekkundi, V. S.; Meghani, P. Tetrahedron Lett. 1990, 31, 3381.
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25. Philp, D.; Robertson, A. Chem. Commun. 1998, 879. Booth, C. A.; Philp, D. Tetrahedron Lett. 1998, 39, 6987. Robertson, A., Philp, D. Tetrahedron 1999, 55, 11365.
26. Page, M. I.; Jencks, W. P. Proc. Natl. Acad. Sci. USA 1971, 68, 1678. Page, M. I. Chem. Soc. Rev. 1973, 2, 295. Kirby, A. J. Adv. Phys. Org. Chem. 1980, 17, 183. Page, M. I. In The Chemistry of Enzyme Action; Page, M. I., Ed.; Elsevier: Amsterdam, 1984; p 1. Menger, F. M. Acc. Chem. Res. 1985, 18, 128. Page, M. I. Philos. Trans. R. Soc. London B 1991, 332, 149. Kirby, A. J. Philos. Trans. R. Soc. London A 1993, 345, 67. Menger, F. M. Acc. Chem. Res. 1993, 26, 206. Bruice, T. C.; Lightstone, F. C. Acc. Chem. Res. 1999, 32, 127.
27. Page, M. I.; Jencks, W. P. Proc. Natl. Acad. Sci. USA 1971, 68, 1678. Page, M. I. Chem. Soc. Rev. 1973, 2, 295. Kirby, A. J. Adv. Phys. Org. Chem. 1980, 17, 183. Page, M. I. In The Chemistry of Enzyme Action; Page, M. I., Ed.; Elsevier: Amsterdam, 1984; p 1. Menger, F. M. Acc. Chem. Res. 1985, 18, 128. Page, M. I. Philos. Trans. R. Soc. London B 1991, 332, 149. Kirby, A. J. Philos. Trans. R. Soc. London A 1993, 345, 67. Menger, F. M. Acc. Chem. Res. 1993, 26, 206. Bruice, T. C.; Lightstone, F. C. Acc. Chem. Res. 1999, 32, 127.
28. Page, M. I.; Jencks, W. P. Proc. Natl. Acad. Sci. USA 1971, 68, 1678. Page, M. I. Chem. Soc. Rev. 1973, 2, 295. Kirby, A. J. Adv. Phys. Org. Chem. 1980, 17, 183. Page, M. I. In The Chemistry of Enzyme Action; Page, M. I., Ed.; Elsevier: Amsterdam, 1984; p 1. Menger, F. M. Acc. Chem. Res. 1985, 18, 128. Page, M. I. Philos. Trans. R. Soc. London B 1991, 332, 149. Kirby, A. J. Philos. Trans. R. Soc. London A 1993, 345, 67. Menger, F. M. Acc. Chem. Res. 1993, 26, 206. Bruice, T. C.; Lightstone, F. C. Acc. Chem. Res. 1999, 32, 127.
29. Page, M. I.; Jencks, W. P. Proc. Natl. Acad. Sci. USA 1971, 68, 1678. Page, M. I. Chem. Soc. Rev. 1973, 2, 295. Kirby, A. J. Adv. Phys. Org. Chem. 1980, 17, 183. Page, M. I. In The Chemistry of Enzyme Action; Page, M. I., Ed.; Elsevier: Amsterdam, 1984; p 1. Menger, F. M. Acc. Chem. Res. 1985, 18, 128. Page, M. I. Philos. Trans. R. Soc. London B 1991, 332, 149. Kirby, A. J. Philos. Trans. R. Soc. London A 1993, 345, 67. Menger, F. M. Acc. Chem. Res. 1993, 26, 206. Bruice, T. C.; Lightstone, F. C. Acc. Chem. Res. 1999, 32, 127.
30. Page, M. I.; Jencks, W. P. Proc. Natl. Acad. Sci. USA 1971, 68, 1678. Page, M. I. Chem. Soc. Rev. 1973, 2, 295. Kirby, A. J. Adv. Phys. Org. Chem. 1980, 17, 183. Page, M. I. In The Chemistry of Enzyme Action; Page, M. I., Ed.; Elsevier: Amsterdam, 1984; p 1. Menger, F. M. Acc. Chem. Res. 1985, 18, 128. Page, M. I. Philos. Trans. R. Soc. London B 1991, 332, 149. Kirby, A. J. Philos. Trans. R. Soc. London A 1993, 345, 67. Menger, F. M. Acc. Chem. Res. 1993, 26, 206. Bruice, T. C.; Lightstone, F. C. Acc. Chem. Res. 1999, 32, 127.
31. Page, M. I.; Jencks, W. P. Proc. Natl. Acad. Sci. USA 1971, 68, 1678. Page, M. I. Chem. Soc. Rev. 1973, 2, 295. Kirby, A. J. Adv. Phys. Org. Chem. 1980, 17, 183. Page, M. I. In The Chemistry of Enzyme Action; Page, M. I., Ed.; Elsevier: Amsterdam, 1984; p 1. Menger, F. M. Acc. Chem. Res. 1985, 18, 128. Page, M. I. Philos. Trans. R. Soc. London B 1991, 332, 149. Kirby, A. J. Philos. Trans. R. Soc. London A 1993, 345, 67. Menger, F. M. Acc. Chem. Res. 1993, 26, 206. Bruice, T. C.; Lightstone, F. C. Acc. Chem. Res. 1999, 32, 127.
32. Page, M. I.; Jencks, W. P. Proc. Natl. Acad. Sci. USA 1971, 68, 1678. Page, M. I. Chem. Soc. Rev. 1973, 2, 295. Kirby, A. J. Adv. Phys. Org. Chem. 1980, 17, 183. Page, M. I. In The Chemistry of Enzyme Action; Page, M. I., Ed.; Elsevier: Amsterdam, 1984; p 1. Menger, F. M. Acc. Chem. Res. 1985, 18, 128. Page, M. I. Philos. Trans. R. Soc. London B 1991, 332, 149. Kirby, A. J. Philos. Trans. R. Soc. London A 1993, 345, 67. Menger, F. M. Acc. Chem. Res. 1993, 26, 206. Bruice, T. C.; Lightstone, F. C. Acc. Chem. Res. 1999, 32, 127.
33. Page, M. I.; Jencks, W. P. Proc. Natl. Acad. Sci. USA 1971, 68, 1678. Page, M. I. Chem. Soc. Rev. 1973, 2, 295. Kirby, A. J. Adv. Phys. Org. Chem. 1980, 17, 183. Page, M. I. In The Chemistry of Enzyme Action; Page, M. I., Ed.; Elsevier: Amsterdam, 1984; p 1. Menger, F. M. Acc. Chem. Res. 1985, 18, 128. Page, M. I. Philos. Trans. R. Soc. London B 1991, 332, 149. Kirby, A. J. Philos. Trans. R. Soc. London A 1993, 345, 67. Menger, F. M. Acc. Chem. Res. 1993, 26, 206. Bruice, T. C.; Lightstone, F. C. Acc. Chem. Res. 1999, 32, 127.
34. Page, M. I.; Jencks, W. P. Proc. Natl. Acad. Sci. USA 1971, 68, 1678. Page, M. I. Chem. Soc. Rev. 1973, 2, 295. Kirby, A. J. Adv. Phys. Org. Chem. 1980, 17, 183. Page, M. I. In The Chemistry of Enzyme Action; Page, M. I., Ed.; Elsevier: Amsterdam, 1984; p 1. Menger, F. M. Acc. Chem. Res. 1985, 18, 128. Page, M. I. Philos. Trans. R. Soc. London B 1991, 332, 149. Kirby, A. J. Philos. Trans. R. Soc. London A 1993, 345, 67. Menger, F. M. Acc. Chem. Res. 1993, 26, 206. Bruice, T. C.; Lightstone, F. C. Acc. Chem. Res. 1999, 32, 127.
35. To distinguish between transition state effects and ground-state effects, we will use the description accelerated when the rate of a reaction is enhanced by the lowering of the energy of the transition state by a recognition event and the description facilitated when the extent of reaction is enhanced by the lowering of the energy of the product by a recognition event.
36. In all cases, only the exo cycloadduct was detected in solution. This is consistent with the tact that the exo adduct is normally the thermodynamic product of furan cyclodaddition reactions.
37. Kinetic simulation and fitting was carried out using Gepasi (version 3.21): Mendes, P. Comput. Appl. Biosci. 1993, 9, 563. Mendes, P. Trends Biochem. Sci. 1997, 22, 361. Mendes P.; Kelll D. B. Bioinformatics 1998. 14, 869).
38. Kinetic simulation and fitting was carried out using Gepasi (version 3.21): Mendes, P. Comput. Appl. Biosci. 1993, 9, 563. Mendes, P. Trends Biochem. Sci. 1997, 22, 361. Mendes P.; Kelll D. B. Bioinformatics 1998. 14, 869).
39. Kinetic simulation and fitting was carried out using Gepasi (version 3.21): Mendes, P. Comput. Appl. Biosci. 1993, 9, 563. Mendes, P. Trends Biochem. Sci. 1997, 22, 361. Mendes P.; Kelll D. B. Bioinformatics 1998. 14, 869).
40. + 169 (9), 123 (51), 44 (100).
41. A suitable comparison compound is 4, in which no intramolecular hydrogen bonding is possible. In compound 4, the amide NH resonance appears at δ 8.67.
42. 2 computer. Conformational searching was earned out using 10 000-step Monte Carlo simulations, and all conformations generated within 50 kJ of the global minimum were minimized.
43. 3OD. The equilibrium constants derived from all of these retro Diels-Alder reactions are in close agreement.
44. -1. We therefore regard the value for the recognition-induced stabilization of 6 stated in the text as a lower limit.