Why a proximity-induced Diels-Alder reaction is so fast

Organic Letters

Volumn 14, Issue 12, 2012, Pages 3016-3019

  Krenske, Elizabeth H ^a   Perry, Emma W ^b   Jerome, Steven V ^b   Maimone, Thomas J ^c   Baran, Phil S ^c   Houk, K N ^b  

^a UNIVERSITY OF MELBOURNE   (Australia)

^b UNIVERSITY OF CALIFORNIA   (United States)

^c SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DITERPENE; VINIGROL;

ARTICLE; CHEMICAL STRUCTURE; CYCLIZATION; SYNTHESIS; TIME;

CYCLIZATION; DITERPENES; MODELS, MOLECULAR; MOLECULAR STRUCTURE; TIME FACTORS;

EID: 84862563892     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol301083q     Document Type: Article

References (22)

1. Maimone, T. J.; Voica, A.-F.; Baran, P. S. Angew. Chem., Int. Ed. 2008, 47, 3054-3056
2. Maimone, T. J.; Shi, J.; Ashida, S.; Baran, P. S. J. Am. Chem. Soc. 2009, 131, 17066-17067
3. Lin, Y.-T.; Houk, K. N. Tetrahedron Lett. 1985, 26, 2269-2272
4. Diedrich, M. K.; Klärner, F.-G.; Beno, B. R.; Houk, K. N.; Senderowitz, H.; Still, W. C. J. Am. Chem. Soc. 1997, 119, 10255-10259
5. Poulin, J.; Grisé-Bard, C. M.; Barriault, L. Angew. Chem., Int. Ed. 2012, 51, 1-5
6. Grisé, C. M.; Tessier, G.; Barriault, L. Org. Lett. 2007, 9, 1545-1548
7. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789
8. Becke, A. D. J. Chem. Phys. 1993, 98, 1372-1377
9. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652
10. Zhao, Y.; Truhlar, D. G. Theor. Chem. Acc. 2008, 120, 215-241
11. Zhao, Y.; Truhlar, D. G. Acc. Chem. Res. 2008, 41, 157-167
12. Barone, V.; Cossi, M. J. Phys. Chem. A 1998, 102, 1995-2001
13. Cossi, M.; Rega, N.; Scalmani, G.; Barone, V. J. Comput. Chem. 2003, 24, 669-681
14. Goldstein, E.; Beno, B.; Houk, K. N. J. Am. Chem. Soc. 1996, 118, 6036-6043
15. Ess, D. H.; Houk, K. N. J. Am. Chem. Soc. 2007, 129, 10646-10647
16. Ess, D. H.; Houk, K. N. J. Am. Chem. Soc. 2008, 130, 10187-10198
17. Hayden, A. E.; Houk, K. N. J. Am. Chem. Soc. 2009, 131, 4084-4089
18. Krenske, E. H.; Houk, K. N.; Holmes, A. B.; Thompson, J. Tetrahedron Lett. 2011, 52, 2181-2184
19. Krenske, E. H.; Davison, E. C.; Forbes, I. T.; Warner, J. A.; Smith, A. L.; Holmes, A. B.; Houk, K. N. J. Am. Chem. Soc. 2012, 134, 2434-2441
20. Paton, R. S.; Kim, S.; Ross, A. G.; Danishefsky, S. J.; Houk, K. N. Angew. Chem., Int. Ed. 2011, 50, 10366-10368
21. Huisgen, R.; Möbius, L.; Müller, G.; Stangl, H.; Szeimies, G.; Vernon, J. M. Chem. Ber. 1965, 98, 3992-4013
22. Huisgen, R.; Ooms, P. H. J.; Mingin, M.; Allinger, N. L. J. Am. Chem. Soc. 1980, 102, 3951-3953