Alkene distortion energies and torsional effects control reactivities, and stereoselectivities of azide cycloadditions to norbornene and substituted norbornenes

Journal of Organic Chemistry

Volumn 78, Issue 5, 2013, Pages 1778-1783

  Lopez, Steven A ^a   Houk, K N ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOADDITION; QUANTUM THEORY; STEREOSELECTIVITY;

1 ,3-DIPOLAR CYCLOADDITIONS; ACTIVATION BARRIERS; DISTORTION ENERGY; NORBORNENE DERIVATIVES; QUANTUM MECHANICAL METHOD; TRANSITION STATE; TRANSITION STATE GEOMETRY; TRANSITION STRUCTURES;

OLEFINS;

ALKENE; CYCLOALKENE; NORBORNENE DERIVATIVE;

ARTICLE; CONFORMATION; CONTROLLED STUDY; CYCLOADDITION; ELECTRON TRANSPORT; ELECTROPHILICITY; ENTHALPY; GEOMETRY; MECHANICAL TORSION; NUCLEOPHILICITY; POLARIZATION; STEREOCHEMISTRY;

EID: 84868119813     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo301267b     Document Type: Article

References (52)

1. Vazquez, S.; Camps, P. Tetrahedron 2005, 61, 5147-5208
2. Sletten, E. M.; Bertozzi, C. R. Acc. Chem. Res. 2011, 44, 666
3. Han, H.-S.; Devaraj, N. K.; Lee, J.; Hilderbrand, S. A.; Weissleder, R.; Bawendi, M. G. J. Am. Chem. Soc. 2010, 132, 7838
4. Huisgen, R.; Moebius, L.; Mueller, G.; Stangl, H.; Szeimies, G.; Vernon, J. M. Chem. Ber. 1965, 98, 3992
5. Gutsmiedl, K.; Wirges, C. T.; Ehmke, V.; Carell, T. Org. Lett. 2009, 11, 2405
6. Hansell, C. F.; Espeel, P.; Stamenovic, M. M.; Barker, I. A.; Dove, A. P.; Du Prez, F. E.; O'Reilly, R. K. J. Am. Chem. Soc. 2011, 133, 13828
7. Watson, W. H.; Galloy, J.; Bartlett, P. D.; Roof, A. A. M. J. Am. Chem. Soc. 1981, 103, 2022
8. Huisgen, R.; Ooms, P. H. J.; Mingin, M.; Allinger, N. L. J. Am. Chem. Soc. 1980, 102, 3951
9. Rondan, N. G.; Paddon-Row, M. N.; Caramella, P.; Mareda, J.; Mueller, P. H.; Houk, K. N. J. Am. Chem. Soc. 1982, 104, 4974
10. Kolb, H. C.; Finn, M. G.; Sharpless, K. B. Angew. Chem., Int. Ed. 2001, 40, 2004
11. Frisch, M. J. (see complete reference in the Supporting Information). Gaussian 09, revision A.1; Gaussian Inc.: Wallingford, CT, 2009.
12. Zhao, Y.; Truhlar, D. G. Theor. Chem. Acc. 2008, 120, 215
13. Grimme, S. J. J. Chem. Phys. 2003, 109, 3067
14. Grimme, S. J. Chem. Phys. 2003, 118, 9095
15. Greenkamp, M.; Grimme, S. Chem. Phys. Lett. 2004, 392, 229
16. Takano, Y.; Houk, K. N. J. Chem. Theor. Comput. 2005, 1, 70
17. Klamt, A.; Schüürmann, G. J. Chem. Soc., Perkin Trans. 2 1993, 799
18. Andzelm, J.; Kolmel, C.; Klamt, A. J. Chem. Phys. 1995, 103, 9312
19. Barone, V.; Cossi, M. J. Phys. Chem. A 1998, 102, 1995
20. Cossi, M.; Rega, N.; Scalmani, G.; Barone, V. J. Comput. Chem. 2003, 24, 669
21. Zhao, Y.; Truhlar, D. G. Phys. Chem. Chem. Phys. 2008, 10, 2813
22. Ribeiro, R. F.; Marenich, A. V.; Cramer, C. J.; Truhlar, D. G. J. Phys. Chem. B. 2011, 115, 14556
23. Lan, Y.; Zou, L.; Cao, Y.; Houk, K. N. J. Phys. Chem. A 2011, 115, 13906
24. Houk, K. N.; Rondan, N. G.; Brown, F. K.; Jorgensen, W. L.; Madura, J. D.; Spellmeyer, D. C. J. Am. Chem. Soc. 1983, 105, 5980
25. Williams, R. V.; Colvin, M. E.; Tran, N.; Warrener, R. N.; Margetić, D J. Org. Chem. 2000, 65, 562
26. Holthausen, M. C.; Koch, W. J. Phys. Chem. 1993, 97, 10021
27. Volland, W. V.; Davidson, E. R.; Borden, W. T. J. Am. Chem. Soc. 1979, 101, 533
28. Williams, R. V.; Margetić, D. J. Org. Chem. 2004, 69, 7134
29. Fernandez, J. A.; Vazquez, S. Eur. J. Org. Chem. 2007, 27, 4493
30. Schleyer, P.; von, R. J. Am. Chem. Soc. 1964, 86, 1854
31. Ess, D. H.; Houk, K. N. J. Am. Chem. Soc. 2007, 129, 10646
32. Wassenaar, J.; Jansen, E.; Zeist, W-J. v.; Bickelhaupt, F. M.; Siegler, M. A.; Spek, A. L.; Reek, J. N. H. Nature Chem. 2010, 2, 417
33. de Jong, G. T.; Bickelhaupt, F. M. ChemPhysChem 2007, 8, 1170
34. Zeist, W-J. v.; Visser, R.; Bickelhaupt, F. M. Chem. Eur. J. 2009, 15, 6112
35. Gordon, C.; Mackey, J. L.; Jewett, J. C.; Sletter, E. M.; Houk, K. N.; Bertozzi, C. R. J. Am. Chem. Soc. 2012, 134, 9199
36. Ess, D. H.; Jones, G. O.; Houk, K. N. Org. Lett. 2008, 10, 1633
37. Huisgen, R.; Moebius, L.; Mueller, G.; Stangl, H.; Szeimies, G.; Vernon, J. M. Chem. Ber. 1965, 98, 3992
38. Watson, W. H.; Galloy, J.; Bartlett, P. D.; Roof, A. A. M. J. Org. Chem. 1985, 50, 4093
39. Ess, D. H.; Houk, K. N. J. Am. Chem. Soc. 2008, 130, 10187
40. Jones, G. O.; Houk, K. N. J. Org. Chem. 2008, 73, 1333
41. Paton, R. S.; Kim, S.; Ross, A. G.; Danishefsky, S. J.; Houk, K. N. Angew. Chem., Int. Ed. 2011, 50, 10366
42. Fernandez, I.; Cossio, F. P.; Bickelhaupt, F.; Matthias J. Org. Chem. 2011, 76, 2310
43. Fernandez, I.; Bickelhaupt, F.; Matthias J. Comput. Chem. 2012, 33, 509
44. Dimroth, O. Angew. Chem. 1933, 46, 571
45. Evans, M. G.; Polanyi, M. Trans. Faraday Soc. 1936, 32, 1340
46. Marcus, R. A. J. Chem. Phys. 1956, 24, 966
47. Hayden, A.; Houk, K. N. J. Am. Chem. Soc. 2009, 131, 4084
48. Osuna, S.; Houk, K. N. Chem.-Eur. J. 2009, 15, 13219
49. Cheong, P. H.-Y.; Paton, R. S.; Bronner, S.; Im, G-Yoon, J.; Garg, N. K.; Houk, K. N. J. Am. Chem. Soc. 2010, 132, 126
50. Yang, J.; Seckute, J.; Cole, C. M.; Devaraj, N. K. Angew. Chem., Int. Ed. 2012, 10.1002/anie.201202122
51. Thalhammer, F.; Wallfahrer, U.; Sauer, J. Tetrahedron Lett. 1990, 31, 3851
52. Sauer, J.; Bäuerlein, P; Ebenbeck, W.; Gousetis, C.; Sichert, H.; Troll, T.; Utz, F.; Wallfahrer, U. Eur. J. Org. Chem. 2001, 2629