Palladium-catalyzed diastereoselective synthesis of isoindolinones

Synthetic Communications

Volumn 27, Issue 23, 1997, Pages 4141-4158

  Cho, C S ^a   Chu, D Y ^a   Lee, D Y ^a   Shim, S C ^a   Kim, T J ^a   Lim, W T ^a   Heo, N H ^a  

^a Kyungpook National University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

ISOINDOLE DERIVATIVE;

ARTICLE; CATALYSIS; CRYSTAL STRUCTURE; CYCLIZATION; DRUG SYNTHESIS; GAS CHROMATOGRAPHY; IN VITRO STUDY; MASS SPECTROMETRY; REACTION ANALYSIS; STEREOCHEMISTRY; X RAY DIFFRACTION;

EID: 0030701879     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1080/00397919708005462     Document Type: Article

References (20)

1. (a) Hegedus, L.S. "Transition Metals in the Synthesis of Complex Organic Molecules," University Science Book, California, 1994.
2. (b) Thebtaranonth, C. and Thebtaranonth, Y. "Cyclization Reaction," CRC Press, London, 1994.
3. (c) Tsuji, J. "Palladium Reagents and Catalysts," Wiley, Chichester, 1995.
4. For the synthesis of isoindolinones via transition metal-catalyzed carbonylative cyclizations: (a) Bird, C.W. J. Organomet. Chem. 1973, 47, 296. (b)Thompson, J.M. and Heck, R.F. J. Org. Chem. 1975, 40, 2667. (c) Mori, M., Chiba, K. and Ban Y. J. Org. Chem. 1978, 43, 1684. (d) Brunet, J.J., Sidot, C. and Caubere, P. J. Org. Chem. 1983, 48, 1166. (e) Shim, S.C., Jiang, L.H., Lee, D.Y. and Cho, C.S. Bull. Korean Chem. Soc. 1995, 16, 1064.
5. For the synthesis of isoindolinones via transition metal-catalyzed carbonylative cyclizations: (a) Bird, C.W. J. Organomet. Chem. 1973, 47, 296. (b)Thompson, J.M. and Heck, R.F. J. Org. Chem. 1975, 40, 2667. (c) Mori, M., Chiba, K. and Ban Y. J. Org. Chem. 1978, 43, 1684. (d) Brunet, J.J., Sidot, C. and Caubere, P. J. Org. Chem. 1983, 48, 1166. (e) Shim, S.C., Jiang, L.H., Lee, D.Y. and Cho, C.S. Bull. Korean Chem. Soc. 1995, 16, 1064.
6. For the synthesis of isoindolinones via transition metal-catalyzed carbonylative cyclizations: (a) Bird, C.W. J. Organomet. Chem. 1973, 47, 296. (b)Thompson, J.M. and Heck, R.F. J. Org. Chem. 1975, 40, 2667. (c) Mori, M., Chiba, K. and Ban Y. J. Org. Chem. 1978, 43, 1684. (d) Brunet, J.J., Sidot, C. and Caubere, P. J. Org. Chem. 1983, 48, 1166. (e) Shim, S.C., Jiang, L.H., Lee, D.Y. and Cho, C.S. Bull. Korean Chem. Soc. 1995, 16, 1064.
7. For the synthesis of isoindolinones via transition metal-catalyzed carbonylative cyclizations: (a) Bird, C.W. J. Organomet. Chem. 1973, 47, 296. (b)Thompson, J.M. and Heck, R.F. J. Org. Chem. 1975, 40, 2667. (c) Mori, M., Chiba, K. and Ban Y. J. Org. Chem. 1978, 43, 1684. (d) Brunet, J.J., Sidot, C. and Caubere, P. J. Org. Chem. 1983, 48, 1166. (e) Shim, S.C., Jiang, L.H., Lee, D.Y. and Cho, C.S. Bull. Korean Chem. Soc. 1995, 16, 1064.
8. For the synthesis of isoindolinones via transition metal-catalyzed carbonylative cyclizations: (a) Bird, C.W. J. Organomet. Chem. 1973, 47, 296. (b)Thompson, J.M. and Heck, R.F. J. Org. Chem. 1975, 40, 2667. (c) Mori, M., Chiba, K. and Ban Y. J. Org. Chem. 1978, 43, 1684. (d) Brunet, J.J., Sidot, C. and Caubere, P. J. Org. Chem. 1983, 48, 1166. (e) Shim, S.C., Jiang, L.H., Lee, D.Y. and Cho, C.S. Bull. Korean Chem. Soc. 1995, 16, 1064.
9. Takahashi, I., Kawakami, T., Hirano, E., Yokota, H. and Kitajima, H. Synlett 1996, 353 and references cited therein.
10. Cho, C.S., Lee, J.W., Lee, D.Y., Shim, S.C. and Kim, T.J. J. Chem. Soc., Chem. Commun. 1996, 2115.
11. (a) Cho, C.S., Jiang, L.H., Lee, D.Y. and Shim, S.C. Bull. Korean Chem. Soc. 1996, 17, 1095.
12. (b) Cho, C.S., Jiang, L.H., Lee, D.Y., Shim, S.C., Lee, H.S. and Cho, S.-D. J. Heterocyclic Chem. in press.
13. 1/2 are 0.0344 and 0.0299, g.o.f. = 0.45.
14. 1/2 are 0.0422 and 0.0445, g.o.f. = 1.42.
15. Main, P., Fiske, S.J., Hull, S.E., Lessinger, L., Germain, G., Declerg, J.P. and Woolfson, M.M. "MULTAN 80," University of York, 1980.
16. "MolEN, An Interactive Structure Solution Procedure," Enraf-Nonius, Delft, The Netherlands, 1990.
17. Coperet, C., Sugihara, G., Wu, G., Shimoyama, I. and Negishi, E. J. Am. Chem. Soc. 1995, 117, 3422.
18. (a) Shim, S.C., Lee, D.Y., Jiang, L.H., Kim, T.J. and Cho, S.-D. J. Heterocyclic Chem. 1995, 52, 363.
19. (b) Marchai, J., Bodiguel, J., Fort, Y. and Caubere, P. J. Org. Chem. 1995, 60, 8336.
20. (c) Lee, D.Y., Cho, C.S., Jiang, L.H., Wu, X., Shim, S.C. and Oh, D.H. Synth. Commun. in press.