Unprecedented Intramolecular [4 + 2]-Cycloaddition between a 1,3-Diene and a Diazo Ester

Journal of the American Chemical Society

Volumn 138, Issue 6, 2016, Pages 1808-1811

  Qiu, Huang ^a,b,c   Srinivas, Harathi D ^a   Zavalij, Peter Y ^b   Doyle, Michael P ^a  

^a UNIVERSITY OF TEXAS AT SAN ANTONIO   (United States)

^b University of Maryland   (United States)

^c EAST CHINA NORMAL UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ESTERS; OLEFINS; PLANTS (BOTANY);

1 ,3-DIENES; DIAZO COMPOUNDS; E-ISOMERS; HIGH YIELD; PROPARGYL; SHORT REACTION TIME; THERMAL REACTIONS; [4 + 2] CYCLOADDITION;

ISOMERS;

CATALYSIS; CYCLOADDITION; ISOMER; REACTION TIME; CHEMICAL STRUCTURE; CHEMISTRY; KINETICS;

ALKENE; ESTER;

ALKENES; CYCLOADDITION REACTION; ESTERS; KINETICS; MOLECULAR STRUCTURE;

EID: 84959017856     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/jacs.5b12877     Document Type: Article

References (38)

1. Hammer, J. 1,4-Cycloaddition Reaction: The Diels-Alder Reaction in Heterocyclic Syntheses; Elsevier: New York, 2013.
2. Carruthers, W. Cycloaddition Reactions in Organic Synthesis; Elsevier: New York, 2013.
3. Nicolaou, K. C.; Snyder, S. A.; Montagnon, T.; Vassilikogiannakis, G. Angew. Chem., Int. Ed. 2002, 41, 1668 10.1002/1521-3773(20020517)41:10<1668::AID-ANIE1668>3.0.CO;2-Z
4. Masson, G. Chem. Soc. Rev. 2013, 42, 902 10.1039/C2CS35370A
5. Pham, H. V.; Houk, K. N. J. Org. Chem. 2014, 79, 8968 10.1021/jo502041f
6. Ma, S. Chem. Rev. 2005, 105, 2829 10.1021/cr020024j
7. Murakami, M.; Itami, K.; Ito, Y. J. Am. Chem. Soc. 1997, 119, 7163 10.1021/ja970626y
8. Wender, P. A.; Jenkins, T. E.; Suzuki, S. J. Am. Chem. Soc. 1995, 117, 1843 10.1021/ja00111a028
9. González, A. Z.; Toste, F. D. Org. Lett. 2010, 12, 200 10.1021/ol902622b
10. Mauleón, P.; Zeldin, R. M.; González, A. Z.; Toste, F. D. J. Am. Chem. Soc. 2009, 131, 6348 10.1021/ja901649s
11. Allen, A. D.; Tidwell, T. T. Chem. Rev. 2013, 113, 7287 10.1021/cr3005263
12. Tidwell, T. T. Ketenes; Wiley: New York, 1995.
13. Brady, W. T.; Agho, M. O. J. Org. Chem. 1983, 48, 5337 10.1021/jo00174a034
14. Bekele, T.; Shah, M. H.; Wolfer, J.; Abraham, C. J.; Weatherwax, A.; Lectka, T. J. Am. Chem. Soc. 2006, 128, 1810 10.1021/ja058077g
15. Abraham, C. J.; Paull, D. H.; Scerba, M. T.; Grebinski, J. W.; Lectka, T. J. Am. Chem. Soc. 2006, 128, 13370 10.1021/ja065754d
16. Huang, X.; He, L.; Shao, P.; Ye, S. Angew. Chem., Int. Ed. 2009, 48, 192 10.1002/anie.200804487
17. Saga, H.; Itoh, K. Methods and Applications of Cycloaddition Reactions in Organic Syntheses; Wiley: New York, 2014.
18. Jiang, N.; Li, C. Chem. Commun. 2004, 40, 394 10.1039/b311763d
19. Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds; John Wiley & Sons Inc.: New York, 1998.
20. Bercovici, D. A.; Ogilvie, J. M.; Tsvetkov, N.; Brewer, M. Angew. Chem., Int. Ed. 2013, 52, 13338 10.1002/anie.201306553
21. Zhang, L. In Contemporary Carbene Chemistry; Moss, R. A.; Doyle, M. P., Eds.; Wiley: New York, 2014; pp 526-551.
22. Wang, Y.; Lackner, A. D.; Toste, F. D. Acc. Chem. Res. 2014, 47, 889 10.1021/ar400188g
23. Shiroodi, R. K.; Dudnik, A. S.; Gevorgyan, V. J. Am. Chem. Soc. 2012, 134, 6928 10.1021/ja301243t
24. Shiroodi, R. K.; Gevorgyan, V. Chem. Soc. Rev. 2013, 42, 4991 10.1039/c3cs35514d
25. Fensterbank, L.; Malacria, M. Acc. Chem. Res. 2014, 47, 953 10.1021/ar4002334
26. Yu, Z.; Ma, B.; Chen, M.; Wu, H.-H.; Liu, L.; Zhang, J. J. Am. Chem. Soc. 2014, 136, 6904 10.1021/ja503163k
27. Ye, L.; Wang, Y.; Aue, D.; Zhang, L. J. Am. Chem. Soc. 2012, 134, 31 10.1021/ja2091992
28. Wang, Y.; Yepremyan, A.; Ghorai, S.; Todd, R.; Aue, D.; Zhang, L. Angew. Chem., Int. Ed. 2013, 52, 7795 10.1002/anie.201301057
29. Zhou, L.; Zhang, M.; Li, W.; Zhang, J. Angew. Chem., Int. Ed. 2014, 53, 6542 10.1002/anie.201403709
30. Burgess, K.; Lim, H.; Porte, A. M.; Sulikowski, G. A. Angew. Chem., Int. Ed. Engl. 1996, 35, 220 10.1002/anie.199602201
31. Briones, J. F.; Davies, H. M. L. J. Am. Chem. Soc. 2012, 134, 11916 10.1021/ja304506g
32. Yu, Z.; Ma, B.; Chen, M.; Wu, H.-H.; Liu, L.; Zhang, J. J. Am. Chem. Soc. 2014, 136, 6904 10.1021/ja503163k
33. Zhang, D.; Xu, G.; Ding, D.; Zhu, C.; Li, J.; Sun, J. Angew. Chem., Int. Ed. 2014, 53, 11070 10.1002/anie.201406712
34. Zhou, L.; Liu, Y.; Zhang, Y.; Wang, J. Beilstein J. Org. Chem. 2011, 7, 631 10.3762/bjoc.7.74
35. Liu, F.; Paton, R. S.; Kim, S.; Liang, Y.; Houk, K. N. J. Am. Chem. Soc. 2013, 135, 15642 10.1021/ja408437u
36. Limanto, J.; Khuong, K. S.; Houk, K. N.; Snapper, M. L. J. Am. Chem. Soc. 2003, 125, 16310 10.1021/ja0380547
37. Tantillo, D. J.; Houk, K. N.; Jung, M. E. J. Org. Chem. 2001, 66, 1938 10.1021/jo001172h
38. Jung, M. E.; Gervay, J. J. Am. Chem. Soc. 1991, 113, 224 10.1021/ja00001a032