Synthesis of 3-vinyl-β-lactams via palladium-catalyzed carbonylative heteroannulation of allylic compounds with imines

Bulletin of the Korean Chemical Society

Volumn 21, Issue 5, 2000, Pages 541-543

  Cho, Chan Sik ^a   Park, Jong Chul ^a   Jiang, Li Hong ^a   Kim, Tae Jeong ^a   Shim, Sang Chul ^a   Kim, Myung Chul ^b  

^a Kyungpook National University   (South Korea)

^b Kyungil University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL COMPOUND; BETA LACTAM DERIVATIVE; IMINE; PALLADIUM;

DRUG STRUCTURE; DRUG SYNTHESIS; NOTE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0013147404     PISSN: 02532964     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Note

References (25)

1. (a) Schore, N. E. Chem. Rev. 1988, 88, 1081.
2. (b) Hegedus, L. S. Angew. Chem., Int. Ed. Engl. 1988, 27, 1113.
3. (c) Colquhiun, H. M.; Tompson, H. M; Twigg, M. V. Carbonylation: Direct Synthesis of Carbonyl Compounds; Plenum Press: New York, 1991.
4. (d) Thebtaranonth, C.; Thebtaranonth, Y. Cyclization Reaction; CRC Press: London, 1994; pp 255-330.
5. (e) Hegedus, L. S. Transition Metals in the Synthesis of Complex Organic Molecules; University Science Book: California, 1994.
6. (f) Tsuji, J. Palladium Reagents and Catalysts; Wiley: Chichester, 1995.
7. (g) Negishi, E.; Coperet, C.; Ma, S.; Liou, S.-Y.; Liu, F. Chem. Rev. 1996, 96, 365.
8. (h) Ojima, I.; Tzamarioudaki, M.; Li, Z. Chem. Rev. 1996, 96, 635.
9. Georg, G. I., Ravikumar, V. T. In The Organic Chemistry of-Lactams; Georg, G. I., Ed.; VCH: New York, 1993; pp 295-368.
10. Examples are cited in ref 7.
11. (a) Torii, S.; Okumoto, H.; Sadakane, M.; Hai, A. K. M. A.; Tanaka, H. Tetrahedron Lett. 1993, 34, 6553.
12. (b) Tanaka, H.; Hai, A. K. M. A.; Sadakane, M.; Okumoto, H.; Torii, S. J. Org. Chem. 1994, 59, 3040.
13. Our series on the palldium-catalyzed carbonylative heteroannulation process for the synthesis of isoindolinones: (a) Cho, C. S.; Jiang, L. H.; Lee, D. Y.; Shim, S. C. Bull. Korean Chem. Soc. 1996, 17, 1095.
14. (b) Cho, C. S.; Lee, J. W.; Lee, D. Y.; Shim, S. C.; Kim, T. J. Chem. Commun. 1996, 2115.
15. (c) Cho, C. S.; Jiang, L. H.; Lee, D. Y.; Shim, S. C.; Lee, H. S.; Cho, S.-D. J. Heterocyclic Chem. 1997, 34, 1371.
16. (d) Cho, C. S.; Chu, D. Y.; Lee, D. Y.; Shim, S. C.; Kim, T. J.; Lim, W. T.; Heo, N. H. Synth. Commun. 1997, 27, 4141.
17. (e) Cho, C. S.; Jiang, L. H.; Shim, S. C. Synth. Commun. 1998, 28, 849.
18. Our series on the palldium-catalyzed carbonylative heteroannulation process for the synthesis of phthalides: (a) Shim, S. C.; Lee, D. Y.; Jiang, L. H.; Kim, T. J.; Cho, S.-D. J. Heterocyclic Chem. 1995, 32, 363.
19. (b) Lee, D. Y.; Cho, C. S.; Jiang, L. H.; Wu, X.; Shim, S. C.; Oh, D. H. Synth. Commun. 1997, 27, 3449.
20. (c) Cho, C. S.; Baek, D. Y.; Shim, S. C. J. Heterocyclic Chem. 1999, 36, 289.
21. Cho, C. S.; Baek, D. Y.; Shim, S. C. J. Heterocyclic Chem. 1999, 36, 1101.
22. (e) Cho, C. S.; Baek, D. Y.; Kim, H.-Y.; Shim, S. C.; Oh, D. H. Synth. Commun. 2000, 30, 1139.
23. Cho, C. S.; Jiang, L. H.; Shim, S. C. Synth. Commun. 1999, 29, 2695.
24. Only one example for the synthesis of 3-vinyl-β-lactam from cinnamyl chloride and N-butylbenzaldimine has been described in ref. 7.
25. Itatani, H.; Bailar, J. C., Jr. J. Am. Oil Chem. Soc. 1967, 44, 147.