Dynamic Effects Responsible for High Selectivity in a [3,3] Sigmatropic Rearrangement Featuring a Bispericyclic Transition State

Journal of Organic Chemistry

Volumn 82, Issue 9, 2017, Pages 4758-4765

  Villar López, Roberto ^a   Faza, Olalla Nieto ^a   Silva López, Carlos ^a  

^a UNIVERSITY OF VIGO   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

POTENTIAL ENERGY; QUANTUM CHEMISTRY;

BISPERICYCLIC TRANSITION STATE; COMPUTATIONAL WORK; DESYM-METRIZATION; DYNAMIC EFFECTS; HIGH SELECTIVITY; SIGMATROPIC REACTIONS; SIGMATROPIC REARRANGEMENTS; TRANSITION STATE;

BIFURCATION (MATHEMATICS);

CARBENE; CYCLOHEXANE; HALOGEN;

ARTICLE; CONFORMATIONAL TRANSITION; COVALENT BOND; ENERGY; HALOGENATION; MOLECULAR DYNAMICS; SURFACE PROPERTY;

EID: 85019038011     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/acs.joc.7b00425     Document Type: Article

References (61)

1. Woodward, R. B.; Hoffmann, R. J. Am. Chem. Soc. 1965, 87, 395-397 10.1021/ja01080a054
2. Woodward, R. B.; Hoffmann, R. Angew. Chem., Int. Ed. Engl. 1969, 8, 781-853 10.1002/anie.196907811
3. Houk, K. N. Stereoselective electrocyclizations and sigmatropic shifts of strained rings: Torquoelectronics. Strain and Its Implications in Organic Chemistry; Kluwer Academic Publishers: Dordrecht, 1989; pp 25-37.
4. Buda, A.; Wang, Y.; Houk, K. J. Org. Chem. 1989, 54, 2264-2266 10.1021/jo00271a003
5. Liang, Y.; Jiao, L.; Zhang, S.; Yu, Z.-X.; Xu, J. J. Am. Chem. Soc. 2009, 131, 1542-1549 10.1021/ja808046e
6. Lecea, B.; Arrieta, A.; Cossío, F. P. J. Org. Chem. 2005, 70, 1035-1041 10.1021/jo048874h
7. Morgan, T. D. R.; LeBlanc, L. M.; Ardagh, G. H.; Boyd, R. J.; Burnell, D. J. J. Org. Chem. 2015, 80, 1042-1051 10.1021/jo502532a
8. López, C. S.; Faza, O. N.; York, D. M.; de Lera, A. J. Org. Chem. 2004, 69, 3635-3644 10.1021/jo049620z
9. Faza, O. N.; Lopez, C. S.; Gonzalez-Perez, A. B.; Perez-Rodriguez, M.; de Lera, A. R. J. Phys. Org. Chem. 2009, 22, 378-385 10.1002/poc.1455
10. Faza, O. N.; López, C. S.; Álvarez, R.; de Lera, A. R. Chem.-Eur. J. 2009, 15, 1944-1956 10.1002/chem.200801133
11. Villar López, R.; Nieto Faza, O.; Silva López, C. RSC Adv. 2015, 5, 30405-30408 10.1039/C5RA01742D
12. Lopez, R. V.; Faza, O. N.; Lopez, C. S. RSC Adv. 2016, 6, 59181-59184 10.1039/C6RA10789C
13. Lenk, W.; Hopf, H. Tetrahedron Lett. 1982, 23, 4073-4076 10.1016/S0040-4039(00)88350-1
14. Hopf, H.; Gottschild, D.; Lenk, W. Isr. J. Chem. 1985, 26, 79-87 10.1002/ijch.198500074
15. Woodward, R.; Katz, T. J. Tetrahedron 1959, 5, 70-89 10.1016/0040-4020(59)80072-7
16. Toma, L.; Romano, S.; Quadrelli, P.; Caramella, P. Tetrahedron Lett. 2001, 42, 5077-5080 10.1016/S0040-4039(01)00891-7
17. Caramella, P.; Quadrelli, P.; Toma, L. J. Am. Chem. Soc. 2002, 124, 1130-1131 10.1021/ja016622h
18. Quadrelli, P.; Romano, S.; Toma, L.; Caramella, P. Tetrahedron Lett. 2002, 43, 8785-8789 10.1016/S0040-4039(02)02014-2
19. Quadrelli, P.; Romano, S.; Toma, L.; Caramella, P. J. Org. Chem. 2003, 68, 6035-6038 10.1021/jo034401j
20. Pham, H.; Houk, K. J. Org. Chem. 2014, 79, 8968-8976 10.1021/jo502041f
21. Yu, P.; Patel, A.; Houk, K. J. Am. Chem. Soc. 2015, 137, 13518-13523 10.1021/jacs.5b06656
22. Singleton, D. A.; Hang, C.; Szymanski, M. J.; Meyer, M. P.; Leach, A. G.; Kuwata, K. T.; Chen, J. S.; Greer, A.; Foote, C. S.; Houk, K. N. J. Am. Chem. Soc. 2003, 125, 1319-1328 10.1021/ja027225p
23. Patel, A.; Chen, Z.; Yang, Z.; Gutiérrez, O.; Liu, H.-W.; Houk, K.; Singleton, D. J. Am. Chem. Soc. 2016, 138, 3631-3634 10.1021/jacs.6b00017
24. Bofill, J. M.; Quapp, W. J. Math. Chem. 2013, 51, 1099-1115 10.1007/s10910-012-0134-3
25. Rehbein, J.; Carpenter, B. K. Phys. Chem. Chem. Phys. 2011, 13, 20906-20922 10.1039/c1cp22565k
26. Collins, P.; Carpenter, B.; Ezra, G.; Wiggins, S. J. Chem. Phys. 2013, 139, 154108 10.1063/1.4825155
27. Zhou, C.; Birney, D. Org. Lett. 2002, 4, 3279-3282 10.1021/ol026595f
28. Sadasivam, D.; Prasad, E.; Flowers, R., II; Birney, D. J. Phys. Chem. A 2006, 110, 1288-1294 10.1021/jp0534075
29. Birney, D. Curr. Org. Chem. 2010, 14, 1658-1668 10.2174/138527210793563260
30. Ess, D.; Wheeler, S.; Iafe, R.; Xu, L.; Çelebi ÖlÇüm, N.; Houk, K. Angew. Chem., Int. Ed. 2008, 47, 7592-7601 10.1002/anie.200800918
31. Suhrada, C. P.; SelÇuki, C.; Nendel, M.; Cannizzaro, C.; Houk, K. N.; Rissing, P.-J.; Baumann, D.; Hasselmann, D. Angew. Chem., Int. Ed. 2005, 44, 3548-3552 10.1002/anie.200500027
32. Reyes, M. B.; Lobkovsky, E. B.; Carpenter, B. K. J. Am. Chem. Soc. 2002, 124, 641-651 10.1021/ja017083j
33. Özkan, I.; Zora, M. J. Org. Chem. 2003, 68, 9635-9642 10.1021/jo035173w
34. Debbert, S. L.; Carpenter, B. K.; Hrovat, D. A.; Borden, W. T. J. Am. Chem. Soc. 2002, 124, 7896-7897 10.1021/ja026232a
35. Samanta, D.; Rana, A.; Schmittel, M. J. Org. Chem. 2014, 79, 2368-2376 10.1021/jo500035b
36. Wang, T.; Hoye, T. Nat. Chem. 2015, 7, 641-645 10.1038/nchem.2281
37. Larson, R.; Pemberton, R.; Franke, J.; Tantillo, D.; Thomson, R. J. Am. Chem. Soc. 2015, 137, 11197-11204 10.1021/jacs.5b07710
38. Thomas, J. B.; Waas, J. R.; Harmata, M.; Singleton, D. A. J. Am. Chem. Soc. 2008, 130, 14544-14555 10.1021/ja802577v
39. Gonzalez-James, O. M.; Kwan, E. E.; Singleton, D. A. J. Am. Chem. Soc. 2012, 134, 1914-1917 10.1021/ja208779k
40. Biswas, B.; Singleton, D. A. J. Am. Chem. Soc. 2015, 137, 14244-14247 10.1021/jacs.5b08635
41. Rehbein, J.; Wulff, B. Tetrahedron Lett. 2015, 56, 6931-6943 10.1016/j.tetlet.2015.10.092
42. Yamataka, H. Molecular Dynamics Simulations and Mechanism of Organic Reactions: Non-TST Behaviors. Advances in Physical Organic Chemistry; Academic Press, 2010; Vol. 44; pp 173-222.
43. Carpenter, B. J. Phys. Org. Chem. 2003, 16, 858-868 10.1002/poc.672
44. Oyola, Y.; Singleton, D. A. J. Am. Chem. Soc. 2009, 131, 3130-3131 10.1021/ja807666d
45. Ussing, B.; Hang, C.; Singleton, D. J. Am. Chem. Soc. 2006, 128, 7594-7607 10.1021/ja0606024
46. Helgaker, T.; Uggerud, E.; Jensen, H. J. A. Chem. Phys. Lett. 1990, 173, 145-150 10.1016/0009-2614(90)80068-O
47. Uggerud, E.; Helgaker, T. J. Am. Chem. Soc. 1992, 114, 4265-4268 10.1021/ja00037a033
48. Bolton, K.; Hase, W. L.; Peslherbe, G. H. Direct Dynamics Simulations of Reactive Systems. Modern Methods for Multidimensional Dynamics Computations in Chemistry; World Scientific: Singapore, 1998; pp 143-189.
49. Peterson, T. H.; Carpenter, B. K. J. Am. Chem. Soc. 1992, 114, 766-767 10.1021/ja00028a057
50. Hohenberg, P.; Kohn, W. Phys. Rev. 1964, 136, B864-B871 10.1103/PhysRev.136.B864
51. Kohn, W.; Sham, L. Phys. Rev. 1965, 140, A1133-A1138 10.1103/PhysRev.140.A1133
52. Zhao, Y.; Truhlar, D. G. Theor. Chem. Acc. 2008, 120, 215-241 10.1007/s00214-007-0310-x
53. Bauernschmitt, R.; Ahlrichs, R. J. Chem. Phys. 1996, 104, 9047-9052 10.1063/1.471637
54. Geuenich, D.; Hess, K.; Kohler, F.; Herges, R. Chem. Rev. 2005, 105, 3758-3772 10.1021/cr0300901
55. Herges, R.; Geuenich, D. J. Phys. Chem. A 2001, 105, 3214-3220 10.1021/jp0034426
56. Keith, T. A.; Bader, R. F. W. Chem. Phys. Lett. 1993, 210, 223-231 10.1016/0009-2614(93)89127-4
57. Chen, W.; Hase, W.; Schlegel, H. Chem. Phys. Lett. 1994, 228, 436-442 10.1016/0009-2614(94)00939-2
58. Millam, J.; Bakken, V.; Chen, W.; Hase, W.; Schlegel, H. J. Chem. Phys. 1999, 111, 3800-3805 10.1063/1.480037
59. Li, X.; Millam, J.; Schlegel, H. J. Chem. Phys. 2000, 113, 10062-10067 10.1063/1.1323503
60. Becker, K.; Parker, J. Randomness. The Guide to Computer Simulations and Games; Wiley: Indianapolis, 2012; pp 119-144.
61. Frisch, M. J. et al. Gaussian09, revision D.01; Gaussian, Inc.: Wallingford, CT, 2013.