Palladium-Mediated 6-endo-trig Intramolecular Cyclization of N-Acryloyl-7-bromoindolines. A Regiochemical Variant of the Intramolecular Heck Reaction

Journal of Organic Chemistry

Volumn 60, Issue 8, 1995, Pages 2312-2313

  Dankwardt, John W ^a   Flippin, Lee A ^a  

^a ROCHE BIOSCIENCE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

INDOLE DERIVATIVE;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029071413     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00113a001     Document Type: Article

References (16)

1. Heck, R. F. Org. React. 1982, 27, 345.
2. Heck, R. F. Palladium Reagents in Organic Synthesis; Academic Press: London, 1985.
3. Heck, R. F. In Compre hensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 4, Chapter 4.3, p 833.
4. de Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379.
5. Cabri, W.; Candiani, I. Acc. Chem. Res. 1995, 28, 2.
6. Grigg, R.; Stevenson, P.; Worakun, T. J. Chem. Soc, Chem. Commun. 1984, 1073.
7. Grigg, R.; Stevenson, P.; Worakun, T. Tetrahedron 1988, 44, 2033.
8. Odie, R.; Blevins, B.; Ratcliff, M.; Hegedus, L. S. J. Org. Chem. 1980, 45, 2709.
9. Negishi, E.; Zhang, Y.; O'Connor, B. Tetrahedron Lett. 1988, 29, 2915. 5-Exo-trig cyclizations:
10. Grigg, R.; Sridharan, V.; Stevenson, P. Tetrahedron 1990, 46, 4003.
11. Larock, R. C.; Babu, S. Tetrahedron Lett. 1987, 28, 5291.
12. Abelman, M. O.; Oh, T.; Overman, L. E. J. Org. Chem. 1987, 52, 4130.
13. Terpko, M. O.; Heck, R. F. J. Am. Chem. Soc. 1979, 101, 5281.
14. Grigg, R.; Sridharan, V.; Stevenson, P.; Worakun, T. J. Chem. Soc, Chem. Commun. 1986, 1697.
15. Ishibashi, H.; Ito, K.; Hirano, T.; Tabuchi, M.; Ikeda, M. Tetrahedron 1993, 49, 4173.
16. Jeffrey, T. J. Chem. Soc, Chem. Commun. 1984, 1287.