Lanthanide triflate-promoted palladium-catalyzed cyclization of alkenyl β-keto esters and amides

Organic Letters

Volumn 5, Issue 16, 2003, Pages 2869-2871

  Yang, Dan ^a   Li, Jin Heng ^a   Gao, Qiang ^a   Yan, Yi Long ^a  

^a UNIVERSITY OF HONG KONG   (Hong Kong)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENYL GROUP; AMIDE; ESTER DERIVATIVE; LANTHANIDE; LANTHANIDE TRIFLATE; LEAD CHLORIDE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CYCLIZATION;

EID: 0141520535     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0349110     Document Type: Article

References (23)

1. (a) Heathcock, C. H.; Graham, S. L.; Pirrung, M. C.; Plavac, W.; White, C. T. In The Total Synthesis of Natural Products; Apsimon, J. W., Ed.; Wiley: New York, 1983; Vol. 5, p 333.
2. (b) Rigby, J. H. In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier Science Publishers B. V.: Amsterdam, 1988; Vol. 12, p 233.
3. (c) Fraga, B. M. Nat. Prod. Rep. 1996, 13, 307.
4. (d) Dyker, G. Angew. Chem., Int. Ed. Engl. 1995, 34, 2223.
5. (a) Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Semmelhack, M. F., Eds.; Pergamon: Oxford, 1991; Vol. 5.
6. (b) Carruthers, W. Cycloaddition Reactions in Organic Synthesis; Pergamon: Oxford, 1990.
7. (c) Hesse, M. Ring Enlargement in Organic Chemistry; VCH: Weinheim, 1991.
8. (d) Renaud, P., Sibi, M. P., Eds. Radicals in Organic Synthesis; Wiley-VCH: Weinheim, 2001.
9. (a) Negishi, E.; Copéret, C.; Ma, S.; Liou, S.-Y.; Liu, F. Chem. Rev. 1996, 96, 365.
10. (b) Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635.
11. (c) Bates, R. W.; Satcharoen, V. Chem. Soc. Roy. 2002, 35, 12.
12. (a) Pei, T.; Widenhoefer, R. A. J. Am. Chem. Soc. 2001, 123, 11290.
13. (b) Pei, T.; Wang, X.; Widenhoefer, R. A. J. Am. Chem. Soc. 2003, 125, 648.
14. (c) Qian, H.; Widenhoefer, R. A. J. Am. Chem. Soc. 2003, 125, 2056.
15. Pei, T.; Widenhoefer, R. A. Chem. Commun. 2002, 650.
16. (a) Yang, D.; Ye, X.-Y.; Gu, S.; Xu, M. J. Am. Chem. Soc. 1999, 121, 5579.
17. (b) Yang, D.; Ye, X.-Y.; Xu, M.; Pang, K.-W.; Cheung, K.-K. J. Am. Chem. Soc. 2000, 122, 1658.
18. (c) Yang, D.; Yan, Y.-L.; Lui, B. J. Org. Chem. 2002, 67, 7429.
19. (d) Yang, D.; Gao, Q.; Lee, C.-S.; Cheung, K.-K. Org. Lett. 2002, 4, 3271.
20. 2, hexane, and toluene.
21. 4. After removal of the solvent, the crude product was purified by flash column chromatography to give 2a (107.8 mg, 99% yield).
22. For the effect of other lanthanide triflates, see Table S1 in Supporting Information.
23. Reetz, M. T.; Chatziiosifidis, I.; Schwellnus, K. Angew. Chem., Int. Ed. Engl. 1981, 20, 687.