Selective monoterpene-like cyclization reactions achieved by water exclusion from reactive intermediates in a supramolecular catalyst

Journal of the American Chemical Society

Volumn 134, Issue 43, 2012, Pages 17873-17876

  Hart Cooper, William M ^a   Clary, Kristen N ^a   Toste, F Dean ^a   Bergman, Robert G ^a   Raymond, Kenneth N ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACIDIC AQUEOUS SOLUTION; CYCLIZATION REACTIONS; CYCLIZATIONS; CYCLOISOMERIZATIONS; ENZYME CATALYSIS; GEM-DIMETHYL; MONOTERPENES; POLYANIONICS; REACTIVE INTERMEDIATE; SUPRAMOLECULAR ASSEMBLIES; SUPRAMOLECULAR CATALYSTS; WATER EXCLUSIONS;

CATALYSIS; CATALYSTS; REACTION INTERMEDIATES; SOLUTIONS;

CYCLIZATION;

CITRONELLAL; WATER;

AQUEOUS SOLUTION; ARTICLE; CATALYSIS; CYCLIZATION; ENCAPSULATION; HYDROPHOBICITY; ISOMERIZATION; SUBSTITUTION REACTION; SUPRAMOLECULAR CHEMISTRY;

ALCOHOLS; CATALYSIS; CYCLIZATION; MACROMOLECULAR SUBSTANCES; MOLECULAR STRUCTURE; WATER;

EID: 84868156148     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja308254k     Document Type: Article

References (43)

1. Köksal, M.; Hu, H.; Coates, R. M.; Peters, R. J.; Christianson, D. W. Nat. Chem. Biol. 2011, 7, 431
2. Christianson, D. W. Chem. Rev. 2006, 106, 3412
3. Faraldos, J. A.; Antonczak, A. K.; González, V.; Fullerton, R.; Tippmann, E. M.; Allemann, R. K. J. Am. Chem. Soc. 2011, 133, 13906
4. Degenhardt, J.; Köllner, T. G.; Gershenzon, J. Phytochemistry 2009, 70, 1621
5. Wheeler, C. J.; Croteau, R. J. Biol. Chem. 1987, 17, 8213
6. Martin, D. M.; Bohlmann, J. Phytochemistry 2004, 65, 1223
7. Hyatt, D. C.; Youn, B.; Zhao, Y.; Santhamma, B.; Coates, R. M.; Croteau, R. B.; Kang, C. Proc. Natl. Acad. Sci. U.S.A. 2007, 104, 5360
8. Avram, L.; Cohen, Y.; Rebek, J., Jr. Chem. Commun. 2011, 47, 5368
9. Purse, B. W.; Rebek, J., Jr. Proc. Natl. Acad. Sci. U.S.A. 2005, 102, 10777
10. Yoshizawa, M.; Klosterman, J. K.; Fujita, M. Angew. Chem., Int. Ed. 2009, 48, 3418
11. Breiner, B.; Clegg, J. K.; Nitschke, J. R. Chem. Sci 2011, 2, 51
12. Weister, M. J.; Ulmann, P. A.; Mirkin, C. A. Angew. Chem., Int. Ed. 2010, 50, 114
13. Meeuwissen, J.; Reek, J. N. H. Nat. Chem 2010, 2, 615 and references therein
14. Hastings, C. J.; Pluth, M. D.; Bergman, R. G.; Raymond, K. N. J. Am. Chem. Soc. 2010, 132, 6938
15. Mock, W. L.; Irra, T. A.; James P. Wepsiec, J. P.; Adhya, M. J. Org. Chem. 1989, 54, 5302
16. Marinescu, L. G.; Bols, M. Angew. Chem., Int. Ed. 2006, 45, 4590
17. Yoon, H. J.; Kuwabara, J.; Kim, J.-H.; Mirkin, C. A. Science 2010, 330, 66
18. Caulder, D. L.; Powers, R. E.; Parac, T. N.; Raymond, K. N. Angew. Chem., Int. Ed. 1998, 37, 1840
19. Reinert, D. J.; Balliano, G.; Schulz, G. E. Chem. Biol. 2004, 11, 121
20. Pluth, M. D.; Bergman, R. G.; Raymond, K. N. J. Am. Chem. Soc. 2007, 129, 11459
21. Pluth, M. D.; Bergman, R. G.; Raymond, K. N. Acc. Chem. Res. 2009, 42, 1650 and references therein
22. Hastings, C. J.; Pluth, M. D.; Bergman, R. G.; Raymond, K. N. J. Am. Chem. Soc. 2010, 132, 6938
23. Hastings, C. J.; Backlund, M. P.; Bergman, R. G.; Raymond, K. N. Angew. Chem., Int. Ed. 2011, 50, 1
24. Lenardao, E. J.; Botteselle, G. V.; de Azambuja, F.; Perin, G.; Jacob, R. G. Tetrahedron 2007, 63, 6671
25. Clark, B. C., Jr.; Chamblee, T. S.; Iacobucci, G. A. J. Org. Chem. 1984, 49, 4557
26. Yuasa, Y.; Tsuruta, H.; Yuasa, Y. Org. Process Res. Dev. 2000, 4, 159
27. Cheng, H.; Meng, X; Liu, R.; Hao, Y.; Yu, Y.; Cai, S.; Zhao, F. Green Chem. 2009, 11, 1227
28. Jung, M. E.; Piizzi, G. Chem. Rev. 2005, 105, 1735 and references therein
29. Jung, M. E. Synlett 1990, 4, 186-190
30. Page, M. J.; Jencks, W. P. Proc. Natl. Acad. Sci. U.S.A. 1971, 68, 1678
31. Bruice, T. C.; Pandit, U. K. Proc. Natl. Acad. Sci. U.S.A. 1960, 46, 402
32. Wang, Z. J.; Brown, C. J.; Bergman, R. G.; Raymond, K. N.; Toste, F. D. J. Am. Chem. Soc. 2011, 133, 7358
33. Watson, I. D. G.; Toste, F. D. Chem. Sci 2012, 3, 2899
34. Núñez-Jiménez, E.; Echavarren, A. M. Chem. Rev. 2008, 108, 3326
35. Michelet, V.; Toullec, P. Y.; Genêt, J. P. Angew. Chem., Int. Ed. 2008, 47, 4268
36. Gorin, D. J.; Toste, F. D. Nature 2007, 446, 395
37. Zhang, L.; Sun, J.; Kozmin, S. A. Adv. Synth. Catal. 2006, 348, 2271
38. For examples of dehydration reactions driven by supramolecular hosts, see: Murase, T.; Nishijima, Y.; Fujita, M. J. Am. Chem. Soc 2012, 134, 162 and references17a and 17b
39. Ferraz, H. M. C.; Grazini, M. V. A.; Ribeiro, C. M. R.; Brocksom, U.; Brocksom, T. J. J. Org. Chem. 2000, 65, 2606
40. Gill, S.; Kocienski, P.; Kohler, A.; Pontiroli, A.; Qun, L. Chem. Commun. 1996, 1743
41. Negoi, A.; Wuttke, S.; Kemnitz, E.; Macovei, D.; Parvulescu, V. I.; Teodorescu, C. M.; Coman, S. M. Angew. Chem., Int. Ed. 2010, 49, 8134
42. Silva, K. A.; Robles-Dutenhefner, P. A.; Sousa, E. M. B.; Kozhevnikova, E. F.; Kozhevnikov, I. V.; Gusevskaya, E. V. Catal. Commun. 2004, 5, 425
43. For an alternative approach to controlling the outcome of terpene cyclization reactions, see: Pronin, V. S.; Shenvi, R. A. Nat. Chem. 2012, 1458