Gold-catalyzed intermolecular reactions of propiolic acids with alkenes: [4 + 2] Annulation and enyne cross metathesis

Journal of the American Chemical Society

Volumn 134, Issue 1, 2012, Pages 208-211

  Yeom, Hyun Suk ^a   Koo, Jaeyoung ^a   Park, Hyun Sub ^a   Wang, Yi ^b   Liang, Yong ^b   Yu, Zhi Xiang ^b   Shin, Seunghoon ^a  

^a Hanyang University   (South Korea)

^b PEKING UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

1 ,3-DIENES; ASYMMETRIC REACTION; BOND REARRANGEMENT; CROSS METATHESIS; CYCLOBUTENE; DFT CALCULATION; INTERMOLECULAR REACTIONS; PROPIOLIC ACID; STEREOSPECIFIC; STEREOSPECIFICITY; STERIC INTERACTIONS;

BUTENES; CATALYSIS; DENSITY FUNCTIONAL THEORY; GOLD;

HYDROCARBONS;

ACID; ALKADIENE; ALKENE; GOLD; LACTONE; PROPIOLIC ACID; UNCLASSIFIED DRUG;

ANNULATION REACTION; ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL REACTION; STEREOSPECIFICITY;

ALKENES; ALKYNES; CATALYSIS; GOLD; PROPIONATES;

EID: 84862933051     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja210792e     Document Type: Article

References (45)

1. Jiménez-Núñez, E.; Echavarren, A. M. Chem. Rev. 2008, 108, 3326
2. Gorin, D. J.; Sherry, B. D.; Toste, F. D. Chem. Rev. 2008, 108, 3351
3. Michelet, V.; Toullec, P. Y.; Genét, J.-P. Angew. Chem., Int. Ed. 2008, 47, 4268
4. Fürstner, A. Chem. Soc. Rev. 2009, 38, 3208
5. Lee, S. I.; Chatani, N. Chem. Commun. 2009, 371
6. Giessert, A. J.; Diver, S. T. Chem. Rev. 2004, 104, 1317
7. Kim, M.; Park, S.; Maifeld, S. V.; Lee, D. J. Am. Chem. Soc. 2004, 126, 10242
8. Kim, M.; Lee, D. Org. Lett. 2005, 7, 1865
9. López-Carrilo, V.; Echavarren, A. M. J. Am. Chem. Soc. 2010, 132, 9292
10. Hashmi, A. S. K.; Blanco, M. C.; Kurpejović, E.; Frey, W.; Bats, J. W. Adv. Synth. Catal. 2006, 348, 709
11. Zhang, L.; Kozmin, S. A. J. Am. Chem. Soc. 2004, 126, 11806
12. Hashmi, A. S. K.; Rudolph, M.; Bats, J. W.; Frey, W.; Rominger, F.; Oeser, T. Chem.-Eur. J. 2008, 14, 6672
13. Li, C.; Zhang, L. Org. Lett. 2011, 13, 1738
14. Kramer, S.; Odabachian, Y.; Overgaard, J.; Rottländer, M.; Gagosz, F.; Skrydstrup, T. Angew. Chem., Int. Ed. 2011, 50, 5090
15. Li, C.-W.; Pati, K.; Lin, G.-Y.; Sohel, S. M. A.; Hung, H.-H.; Liu, R.-S. Angew. Chem., Int. Ed. 2010, 49, 9891
16. Davies, P. W.; Cremonesi, A.; Martin, N. Chem. Commun. 2011, 47, 379
17. Davies, P. W.; Cremonesi, A.; Dumitrescu, L. Angew. Chem., Int. Ed. 2011, 50, 8931
18. Dateer, R. B.; Shaibu, B. S.; Liu, R.-S.; Angew. Chem., Int. Ed. 2011, 50, DOI: 10.1002/anie.201105921.
19. Shi, Z.; He, C. J. Org. Chem. 2004, 69, 3669
20. Haro, T.; Nevado, C. J. Am. Chem. Soc. 2010, 132, 1512
21. Luo, T.; Dai, M.; Zhang, S.-L.; Schreiber, S. L. Org. Lett. 2011, 13, 2834
22. Trost, B. M.; Ganoury, G. J. J. Am. Chem. Soc. 1988, 110, 1636
23. Chatani, N.; Morimoto, T.; Muto, T.; Murai, S. J. Am. Chem. Soc. 1994, 116, 6049
24. Fürstner, A.; Szillat, H.; Gabor, B.; Mynott, R. J. Am. Chem. Soc. 1998, 120, 8305
25. Chatani, N.; Inoue, H.; Kotsuma, T.; Murai, S. J. Am. Chem. Soc. 2002, 124, 10294
26. Méndez, M.; Muñoz, M. P.; Echavarren, A. M. J. Am. Chem. Soc. 2000, 122, 11549
27. Nieto-Oberhuber, C.; Muñoz, M. P.; Buñuel, E.; Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. Angew. Chem., Int. Ed. 2004, 43, 2402
28. Buck, S. B.; Hardouin, C.; Ichikawa, S.; Soenen, D. R.; Gauss, C.-M.; Hwang, I.; Swingle, M. R.; Bonness, K. M.; Honkanen, R. E.; Boger, D. L. J. Am. Chem. Soc. 2003, 125, 15694
29. BouzBouz, S.; Cossy, J. Org. Lett. 2003, 5, 1995
30. Terada, M.; Mikami, K.; Nakai, T. Tetrahedron Lett. 1991, 32, 935
31. Kang, J.-E.; Lee, E.-S.; Park, S.-I.; Shin, S. Tetrahedron Lett. 2005, 46, 7431
32. Kang, J.-E.; Shin, S. Synlett 2006, 717
33. Lim, C.; Kang, J.-E.; Lee, E. S.; Shin, S. Org. Lett. 2007, 9, 3539
34. Fürstner, A.; Morency, L. Angew. Chem., Int. Ed. 2008, 47, 5030
35. Crone, B.; Kirsch, S. F.; Umland, K.-D. Angew. Chem., Int. Ed. 2010, 49, 4661
36. In contrast, in gold-catalyzed domino cyclizations of 1,n-enynes followed by trapping with external nucleophiles, C-C and C-Nu bonds typically form with net anti- addition with respect to an alkene: Pradal, A.; Chao, C.-M.; Vitale, M. R.; Toullec, P. Y.; Genét, J.-P. Tetrahedron 2011, 67, 4371
37. Kim, S. M.; Park, J. H.; Choi, S. Y.; Chung, Y. K. Angew. Chem., Int. Ed. 2007, 46, 6172
38. Johansson, M. J.; Gorin, D. J.; Staben, S. T.; Toste, F. D. J. Am. Chem. Soc. 2005, 127, 18002
39. Hashmi, A. S. K.; Hamzic, M.; Rominger, F.; Bats, J. W. Chem.-Eur. J. 2009, 15, 13318
40. Pradal, A.; Toullec, P. Y.; Michelet, V. Synthesis 2011, 1501
41. Dolbier, W. R.; Koroniak, H.; Houk, K. N.; Sheu, C. Acc. Chem. Res. 1996, 29, 471
42. Um, J. M.; Xu, H.; Houk, K. N.; Tang, W. J. Am. Chem. Soc. 2009, 131, 6664
43. Liang, Y.; Jiao, L.; Zhang, S.; Yu, Z.-X.; Xu, J. J. Am. Chem. Soc. 2009, 131, 1542
44. Snider, B. B.; Rodini, D. J.; Conn, R. S. E.; Sealfon, S. J. Am. Chem. Soc. 1979, 101, 5283
45. Xu, H.; Zhang, W.; Shu, D.; Werness, J. B.; Tang, W. Angew. Chem., Int. Ed. 2008, 47, 8933