Intramolecular aryne-ene reaction: Synthetic and mechanistic studies

Journal of the American Chemical Society

Volumn 133, Issue 36, 2011, Pages 14200-14203

  Candito, David A ^a   Panteleev, Jane ^a   Lautens, Mark ^a  

^a UNIVERSITY OF TORONTO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ENE REACTION; HETEROCYCLES; MECHANISTIC DATA; MECHANISTIC STUDIES;

STEREOCHEMISTRY;

SYNTHESIS (CHEMICAL);

ARYNE; CHEMICAL COMPOUND; ENE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; MOLECULAR MECHANICS; STEREOCHEMISTRY; SYNTHESIS;

ORGANIC CHEMICALS;

EID: 80052598707     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja205405n     Document Type: Article

References (29)

1. Dyke, A. M.; Hester, A. J.; Lloyd-Jones, G. C. Synthesis 2006, 4093
2. Chen, Y.; Larock, R. C. In Modern Arylation Methods; Akermann, L., Ed.; Wiley-VCH: Weinheim, 2009; pp 401-473.
3. Sanz, R. Org. Prep. Proced. Int. 2008, 40, 215
4. Pellissier, H.; Santelli, M. Tetrahedron 2003, 59, 701
5. Hoffmann, R. W. Dehydrobenzene and Cycloalkynes; Academic Press: New York, 1967.
6. Gilchrist, T. L. In Science of Synthesis; Hopf, H., Ed.; Georg Thieme Verlag KG: Stuttgart, 2011; pp 151-203.
7. Dockendorff, C.; Sahli, S.; Olsen, M.; Milhau, L.; Lautens, M. J. Am. Chem. Soc. 2005, 127, 15028
8. Webster, R.; Lautens, M. Org. Lett. 2009, 11, 4688
9. Aly, A. A.; Mohamed, N. K.; Hassan, A. A.; Mourad, A.-F. E. Tetrahedron 1999, 55, 1111
10. Jayanth, T. T.; Jeganmohan, M.; Cheng, M.-J.; Chu, S.-Y.; Cheng, C.-H. J. Am. Chem. Soc. 2006, 128, 2232
11. Friedman, L.; Osiewicz, R. J.; Rabideau, P. W. Tetrahedron Lett. 1968, 5735
12. Ahlgren, G.; Akermark, B. Tetrahedron Lett. 1970, 3047
13. Wasserman, H. H.; Solodar, A. J.; Keller, L. S. Tetrahedron Lett. 1968, 5597
14. Garsky, V.; Koster, D. F.; Arnold, R. T. J. Am. Chem. Soc. 1974, 96, 4207
15. Wasserman, H. H.; Keller, L. S. Tetrahedron Lett. 1974, 4355
16. Aly, A. A.; Shaker, R. M. Tetrahedron Lett. 2005, 46, 2679
17. Nakayama, J.; Yoshimura, K. Tetrahedron Lett. 1994, 35, 2709
18. Tabushi, I.; Okazaki, K.; Oda, R. Tetrahedron 1969, 25, 4401
19. Crews, P.; Beard, J. J. Org. Chem. 1973, 38, 522
20. Hayes, M. E.; Shinokubo, H.; Danheiser, R. L. Org. Lett. 2005, 7, 3917
21. Buszek, K. R. Tetrahedron Lett. 1995, 36, 9125
22. Buszek, K. R.; Bixby, D. L. Tetrahedron Lett. 1995, 36, 9129
23. Chen, C.-L.; Sparks, S. M.; Martin, S. F. J. Am. Chem. Soc. 2006, 128, 13696
24. Uchiyama, M.; Miyoshi, T.; Kajihara, Y.; Sakamoto, T.; Otani, Y.; Ohwada, T.; Kondo, Y. J. Am. Chem. Soc. 2002, 124, 8514
25. Deppmeier, B. J. SPARTAN '08 build 132; Wavefunction Inc.: Sales: Irvine, CA, 1995. Calculations were performed using Spartan '08 V1.2.0. Geometry optimizations were carried out at B3LYP/6-31G* level of theory. Frequency calculations were used to characterize stationary points as minima or transition states. See the Supporting Information.
26. Cheong, P. H.-Y.; Paton, R. S.; Bronner, S. M.; Im, G.-Y. J.; Garg, N. K.; Houk, K. N. J. Am. Chem. Soc. 2010, 132, 1267
27. Im, G.-Y. J.; Bronner, S. M.; Goetz, A. E.; Paton, R. S.; Cheong, P. H.-Y.; Houk, K. N.; Garg, N. K. J. Am. Chem. Soc. 2010, 132, 17933
28. Garr, A. N.; Luo, D.; Brown, N.; Cramer, C. J.; Buszek, K. R.; Van der Velde, D. Org. Lett. 2010, 12, 96
29. Snieckus, V. Chem. Rev. 1990, 90, 879