AuCl3-catalyzed synthesis of highly substituted furans from 2-(1-alkynyl)-2-alken-1-ones

Journal of the American Chemical Society

Volumn 126, Issue 36, 2004, Pages 11164-11165

  Yao, Tuanli ^a   Zhang, Xiaoxia ^a   Larock, Richard C ^a  

^a IOWA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 PHENYLETHYNYL 2 CYCLOHEXEN 1 ONE; 3 PHENYL 2 PROPYN 1 OL; ALCOHOL DERIVATIVE; ALKYNE; ALLENE DERIVATIVE; DIHYDRORESORCINOL; FURAN DERIVATIVE; GOLD CHLORIDE; KETONE DERIVATIVE; METHANOL; PALLADIUM; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHEMICAL BOND; CYCLIZATION; ELECTRON; ORGANIC CHEMISTRY; PROTON TRANSPORT; SYNTHESIS;

EID: 4544255270     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0466964     Document Type: Article

References (24)

1. (a) Dean, F. A. Naturally Occurring Oxygen Ring Compounds; Butterworth: London, 1963.
2. (b) Natural Products Chemistry, Nakanishi, K., Goto, T., Ito, S., Natori, S., Nozoe, S., Eds.: Kodansha: Tokyo, 1974; Vols. 1-3.
3. (c) Dean, F. M. In Advances in Heterocyclic Chemistry; Katritzky, A. R., Ed.; Academic Press: New York, 1983; Vol. 31, pp 237-344.
4. (d) Sargent, M. V.; Dean, F. M. In Comprehensive Heterocyclic Chemistry; Bird, C. W., Cheeseman, G. W. H., Eds.; Pergamon Press: Oxford. 1984; Vol. 3, pp 599-656.
5. (e) Lipshutz, B. H. Chem. Rev. 1986, 86, 795-819.
6. (a) Benassi, R. In Comprehensive Heterocyclic Chemistry II; Katritzky. A. R., Rees, C. W., Scriven, E. F. V., Eds.; Pergamon Press: Oxford, 1996; Vol. 2, pp 259-295.
7. (b) Heaney, H.; Ahn, J. S. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Eds.: Pergamon Press: Oxford, 1996; Vol. 2, pp 297-357.
8. (c) Friedrichsen, W. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Pergamon Press: Oxford, 1996; Vol. 2, pp 351-393.
9. (d) Keay, B. A., Dibble, P. W. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Pergamon Press: Oxford, 1996; Vol. 2, pp 395-436.
10. (e) Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991.
11. Recent reviews: (a) Hou, X. L.; Yang, Z.; Wong, H. N. C. In Progress in Heterocyclic Chemistry; Gribble, G. W., Gilchrist, T. L., Eds.; Pergamon Press: Oxford, 2002; Vol. 14, pp 139-179.
12. (b) Cacchi, S. J. Organomet. Chem. 1999, 576, 42-64.
13. (c) Hou, X. L.; Cheung, H. Y.; Hon, T. Y.; Kwan, P. L.; Lo, T. H.; Tong, S. Y.; Wong, H. N. C. Tetrahedron 1998, 54, 1955-2020.
14. (a) Hashmi, A. S. K.; Schwarz, L.; Choi, J.-H.; Frost, T. M. Angew. Chem., Int. Ed. 2000, 39, 2285-2288.
15. (b) Marshall, J. A.; Bartley, G. S. J. Org. Chem. 1994, 59, 7169-7171.
16. (c) Marshall, J. A.; Wang, X.-J. J. Org. Chem. 1991, 56, 960-969.
17. (d) Fukuda, Y.; Shiragami, H.; Utimoto, K.; Nozaki, H. J. Org. Chem. 1991, 56, 5816-5819.
18. (e) Kel'in, A. V.; Gevorgyan, V. J. Org. Chem. 2002, 67, 95-98.
19. Hashmi, A. S. K.; Bats, J. W.; Choi, J.-H.; Schwarz, L. Tetrahedron Lett. 1998, 39, 7491-7494.
20. Trost, B. M. Science 1991, 254, 1471-1477.
21. Ferreira, E. M.; Stoltz, B. M. J. Am. Chem. Soc. 2003, 125, 9578-9579 and references therein.
22. Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 7894-7895.
23. Abbiati, G.; Arcadi, A.; Bianchi, G.; Di Giuseppe, S.; Marinelli, F.; Rossi, E. E. J. Org. Chem. 2003, 68, 6959-6966.
24. Kobayashi, S.; Kakumoto, K.; Sugiura, M. Org. Lett. 2002, 4, 1319-1322.