Diels-Alder reactivities of strained and unstrained cycloalkenes with normal and inverse-electron-demand dienes: Activation barriers and distortion/interaction analysis

Journal of the American Chemical Society

Volumn 135, Issue 41, 2013, Pages 15642-15649

  Liu, Fang ^a   Paton, Robert S ^b   Kim, Seonah ^a   Liang, Yong ^a   Houk, K N ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b UNIVERSITY OF OXFORD   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVATION BARRIERS; DIELS-ALDER REACTION; DIELS-ALDER TRANSITION STATE; DISTORTION ENERGY; EXPERIMENTAL VALUES; FAVORABLE INTERACTIONS; INTERACTION ENERGIES; QUANTUM-MECHANICAL CALCULATION;

CHEMICAL REACTIONS; PROPYLENE;

ACTIVATION ANALYSIS;

1,3 DIMETHOXYBUTADIENE; 3,6 BIS(TRIFLUOROMETHYL)TETRAZINE; 3,6 DIMETHYLTETRAZINE; ALKADIENE; CYCLOALKENE; CYCLOHEXENE DERIVATIVE; CYCLOPENTADIENE; CYCLOPROPENE; PROPYLENE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; DIELS ALDER REACTION;

EID: 84886925222     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja408437u     Document Type: Article

References (51)

1. Paton, R. S.; Kim, S.; Ross, A. G.; Danishefsky, S. J.; Houk, K. N. Angew. Chem., Int. Ed. 2011, 50, 10366
2. van Zeist, W.-J.; Bickelhaupt, F. M. Org. Biomol. Chem. 2010, 8, 3118
3. Ess, D. H.; Houk, K. N. J. Am. Chem. Soc. 2007, 129, 10646
4. Ess, D. H.; Houk, K. N. J. Am. Chem. Soc. 2008, 130, 10187
5. Fernández, I.; Cossío, F. P.; Bickelhaupt, F. M. J. Org. Chem. 2011, 76, 2310
6. Lan, Y.; Wheeler, S. E.; Houk, K. N. J. Chem. Theory Comput. 2011, 7, 2104
7. Fernández, I.; Bickelhaupt, F. M. J. Comput. Chem. 2012, 33, 509
8. Gordon, C. G.; Mackey, J. L.; Jewett, J. C.; Sletten, E. M.; Houk, K. N.; Bertozzi, C. R. J. Am. Chem. Soc. 2012, 134, 9199
9. Liang, Y.; Mackey, J. L.; Lopez, S. A.; Liu, F.; Houk, K. N. J. Am. Chem. Soc. 2012, 134, 17904
10. Fernández, I.; Bickelhaupt, F. M.; Cossío, F. P. Chem.-Eur. J. 2012, 18, 12395
11. Lopez, S. A.; Houk, K. N. J. Org. Chem. 2013, 78, 1778
12. Fernández, I.; Sola, M.; Bickelhaupt, F. M. Chem.-Eur. J. 2013, 19, 7416
13. Rubin, M.; Rubina, M.; Gevorgyan, V. Synthesis 2006, 1221
14. Zhu, Z.-B.; Wei, Y.; Shi, M. Chem. Soc. Rev. 2011, 40, 5534
15. Wilson, M. R.; Taylor, R. E. Angew. Chem., Int. Ed. 2013, 52, 4078
16. Patterson, D. M.; Nazarova, L. A.; Xie, B.; Kamber, D. N.; Prescher, J. A. J. Am. Chem. Soc. 2012, 134, 18638
17. Kamber, D. N.; Nazarova, L. A.; Liang, Y.; Lopez, S. A.; Patterson, D. M.; Shih, H.-W.; Houk, K. N.; Prescher, J. A. J. Am. Chem. Soc. 2013, 135, 13680
18. Yang, J.; Šečkute, J.; Cole, C. M.; Devaraj, N. K. Angew. Chem., Int. Ed. 2012, 51, 7476
19. Cole, C. M.; Yang, J.; Šečkute, J.; Devaraj, N. K. ChemBioChem 2013, 14, 205
20. Šečkute, J.; Yang, J.; Devaraj, N. K. Nucleic Acids Res. 2013, 41, e148
21. Yu, Z.; Pan, Y.; Wang, Z.; Wang, J.; Lin, Q. Angew. Chem., Int. Ed. 2012, 51, 10600
22. Wiberg, K. B.; Bartley, W. J. J J. Am. Chem. Soc. 1960, 82, 6375
23. Lou, Y.; Horikawa, M.; Kloster, R. A.; Hawryluk, N. A.; Corey, E. J. J. Am. Chem. Soc. 2004, 126, 8916
24. Cadogan, J. I. G.; Cameron, D. K.; Gosney, I.; Tinley, E. J.; Wyse, S. J.; Amaro, A. J. Chem. Soc., Perkin Trans. 1 1991, 2081
25. Brúson, H. A.; Riener, T. W. J. Am. Chem. Soc. 1945, 67, 723
26. Thalhammer, F.; Wallfahrer, U.; Sauer, J. Tetrahedron Lett. 1990, 31, 6851
27. Wolk, J. L.; Rozental, E.; Basch, H.; Hoz, S. J. Org. Chem. 2006, 71, 3876
28. Roberts, J. D.; Caserio, M. C. Basic Principles of Organic Chemistry, 2 nd ed.; W. A. Benjamin, Inc.: Menlo Park, CA, 1997.
29. Schoenebeck, F.; Ess, D. H.; Jones, G. O.; Houk, K. N. J. Am. Chem. Soc. 2009, 131, 8121
30. Hayden, A. E.; Houk, K. N. J. Am. Chem. Soc. 2009, 131, 4084
31. Frisch, M. J., Gaussian 09, revision C.01; Gaussian, Inc.: Wallingford, CT, 2010.
32. Zhao, Y.; Truhlar, D. G. Theor. Chem. Acc. 2008, 120, 215
33. Zhao, Y.; Truhlar, D. G. Acc. Chem. Res. 2008, 41, 157
34. Lan, Y.; Zou, L.; Cao, Y.; Houk, K. N. J. Phys. Chem. A 2011, 115, 13906
35. Paton, R. S.; Mackey, J. L.; Kim, W. H.; Lee, J. H.; Danishefsky, S. J.; Houk, K. N. J. Am. Chem. Soc. 2010, 132, 9335
36. Zhao, Y.; Truhlar, D. G. Phys. Chem. Chem. Phys. 2008, 10, 2813
37. Ribeiro, R. F.; Marenich, A. V.; Cramer, C. J.; Truhlar, D. G. J. Phys. Chem. B 2011, 115, 14556
38. Barone, V.; Cossi, M. J. Phys. Chem. A 1998, 102, 1995
39. Cossi, M.; Rega, N.; Scalmani, G.; Barone, V. J. Comput. Chem. 2003, 24, 669
40. Glendening, E. D.; Reed, A. E.; Carpenter, J. E.; Weinhold, F. NBO, version 3.1; University of Wisconsin: Madison, WI, 1996.
41. Ringer, A. L.; Figgs, M. S.; Sinnokrot, M. O.; Sherrill, C. D. J. Phys. Chem. A 2006, 110, 10822
42. Maity, S.; Sedlak, R.; Hobza, P.; Patwari, G. N. Phys. Chem. Chem. Phys. 2009, 11, 9738
43. Politzer, P.; Abu-Awwad, F. Theor. Chem. Acc. 1998, 99, 83
44. Kar, T.; Angyan, J. G.; Sannigrahi, A. B. J. Phys. Chem. A 2000, 104, 9953
45. Zhang, G.; Musgrave, C. B. J. Phys. Chem. A 2007, 111, 1554
46. Rademacher, P. Chem. Rev. 2003, 103, 933
47. Staley, S. W.; Howard, A. E.; Strnad, J. T. J. Org. Chem. 1992, 57, 895
48. Mitchell, R. W.; Dorko, E. A.; Merritt, J. A. J. Mol. Spectrosc. 1968, 26, 197
49. Craig, N. C.; Borick, S. S.; Tucker, T. R.; Xiao, Y.-Z. J. Phys. Chem. 1991, 95, 3549
50. Villarreal, J. R.; Laane, J. Spectrochim. Acta 1979, 35, 331
51. Neto, N.; Di Lauro, C. Spectrochim. Acta 1967, 23, 1763