Efficient and reusable PdCl2(MeCN)2/CuCl 2/PEG-400 system for cyclization of alkenyl β-keto esters and amides

Journal of Organic Chemistry

Volumn 70, Issue 13, 2005, Pages 5347-5349

  Li, Jin Heng ^a   Zhu, Qi Ming ^a   Liang, Yun ^a   Yang, Dan ^b  

^a HUNAN NORMAL UNIVERSITY   (China)

^b UNIVERSITY OF HONG KONG   (Hong Kong)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLATION; AMINES; ESTERS; KETONES; POLYETHYLENE GLYCOLS; RECYCLING;

Β-KETO ESTERS; AMIDES; CYCLIZATION REACTIONS; HYDROALKYLATION;

PALLADIUM COMPOUNDS;

AMIDE; ESTER; MACROGOL 400; TRANSITION ELEMENT;

ALKYLATION; ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHROMATOGRAPHY; CYCLIZATION; MOLECULAR INTERACTION; STOICHIOMETRY; SYNTHESIS;

EID: 20844462727     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0506635     Document Type: Article

References (25)

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 E.V.: Amsterdam, The Netherlands, 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, UK, 1991; Vol. 5.
6. (b) Carruthers, W. Cycloaddition Reactions in Organic Synthesis; Pergamon: Oxford, UK, 1990.
7. (c) Hesse, M. Ring Enlargement in Organic Chemistry; VCH: Weinheim, Germany, 1991.
8. (d) Renaud, P.; Sibi, M. P., Eds. Radicals in Organic Synthesis; Wiley-VCH: Weinheim, Germany, 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. Rev. 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. (d) Pei, T.; Widenhoefer, R. A. Chem. Commun, 2002, 650.
16. (e) Han, X.; Wang, X.; Pei, T.; Widenhoefer, R. A. Chem. Eur. J. 2004, 10, 6333.
17. Yang, D.; Li, J.-H.; Gao, Q.; Yan, Y.-L. Org. Lett. 2003, 5, 2869.
18. For selected representative papers on PEG as the media, see: (a) Santaniello, E.; Manzocchi, A.; Sozzani, P. Tetrahedron. Lett. 1979, 20, 4581.
19. (b) Santaniello, E.; Fiecchi, A.; Manzocchi, A.; Ferraboschi, P. J. Org. Chem. 1983, 48, 3074.
20. (c) Chandrasehar, S.; Narsihmulu, Ch.; Sultana, S. S.; Reddy, N. R. K. Org. Lett. 2002, 4, 4399 and references therein.
21. (d) Chandrasehar, S.; Narsihmulu, Ch.; Sultana, S. S.; Reddy, N. R. K. Chem. Commun. 2002, 1716.
22. (e) Chandrasehar, S.; Narsihmulu, Ch.; Saritha, B.; Sultana, S. S. Tetrahedron. Lett. 2004, 45, 5865 and references therein.
23. Reetz, M. T.; Chatziiosidis, I.; Schwellnus K. Angew. Chem., Int. Ed. Engl. 1981, 20, 687.
24. No cyclization reaction of substrates 1c occurred due to the unfavorable steric hindrance, and the reaction of 1i or 1k was not successful presumably because the olefins 1i and 1k bind less tightly to transient metals. See: (a) Hartley, F. R. Chem. Rev. 1973, 73, 163.
25. (b) References 4 and 7.