Direct N-carbamoylation of 3-monosubstituted oxindoles with alkyl imidazole carboxylates

Journal of Organic Chemistry

Volumn 74, Issue 14, 2009, Pages 5115-5117

  Trost, Barry M ^a   Zhang, Yong ^a   Zhang, Ting ^a  

^a STANFORD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBAMOYL; CARBAMOYLATION; CHEMICAL EQUATIONS; OXINDOLES; REGIO-SELECTIVE;

CARBOXYLATION;

ALKYL GROUP; CARBOXYLIC ACID; IMIDAZOLE; OXINDOLE;

ACYLATION; ALKYLATION; ARTICLE; CARBAMOYLATION; CATALYSIS; CHEMICAL REACTION; GRIGNARD REACTION; HYDROGENATION;

CARBOXYLIC ACIDS; IMIDAZOLES; INDOLES; MOLECULAR STRUCTURE; NITROGEN; OXIDATION-REDUCTION; STEREOISOMERISM;

EID: 67650355484     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo900760r     Document Type: Article

References (32)

1. (a) Lebsack, A. D.; Link, J. T.; Overman, L. E.; Stean, B. A. J. Am. Chem. Soc. 2002, 124, 9008.
2. (b) Lakshmaiah, G.; Kawabata, T.; Shang, M.; Fuji, K. J. Org. Chem. 1999, 64, 1699.
3. (c) Trost, B. M.; Brennan, M. K. Org. Lett. 2006, 8, 2027.
4. (d) Overman, L. E.; Shin, Y. Org. Lett. 2007, 9, 339.
5. (e) Trost, B. M.; Stiles, D. T. Org. Lett. 2007, 9, 2763.
6. (a) Trost, B. M.; Frederiksen, M. U. Angew. Chem., Int. Ed. 2005, 44, 308.
7. (b) Trost, B. M.; Zhang, Y. J. Am. Chem. Soc. 2006, 128, 4590.
8. (c) Trost, B. M.; Zhang, Y. J. Am. Chem. Soc. 2007, 129, 14548.
9. (a) Shaw, S. A.; Aleman, P.; Vedeis, E. J. Am. Chem. Soc. 2003, 125, 13368.
10. (b) Hills, I. D.; Fu, G. C. Angew. Chem. Int. Ed. 2003, 42, 3921.
11. (a) Hamashima, Y.; Suzuki, T.; Takano, H.; Shimura, Y.; Sedeoka, M. J. Am. Chem. Soc. 2005, 127, 10164.
12. (b) Ishimaru, T.; Shibata, N.; Horikawa, T.; Yasuda, N.; Nakamura, S.; Toru, T.; Shiro, M. Angew. Chem., Int. Ed. 2008, 47, 4157.
13. (a) Ishimaru, T.; Shibata, N.; Nagai, J.; Nakamura, S.; Toru, T.; Kanemasa, S. J. Am. Chem. Soc. 2006, 128, 16488.
14. (b) Sano, D.; Nagata, K.; Itoh, T. Org. Lett. 2008, 10, 1593.
15. (a) Ogawa, S.; Shibata, N.; Inagaki, J.; Nakamura, S.; Toru, T.; Shiro, M. Angew. Chem., Int. Ed. 2007, 46, 8666.
16. (b) Tian, X.; Jiang, K.; Peng, J.; Du, W.; Chen, Y.-C. Org. Lett. 2008, 10, 3583.
17. Linton, E. C.; Kozlowski, M. C. J. Am. Chem. Soc. 2008, 130, 16162.
18. Corey, E. J.; Bock, M. G.; Kozikowski, A. P.; Rao, A. V. R.; Floyd, D.; Lipshutz, B. Tetrahedron Lett. 1978, 1051.
19. Our group has recently reported the use of N-Moc-3-alkylideneoxindoles as substrates for asymmetric TMM reactions: Trost, B. M.; Cramer, N.; Silverman, S. M. J. Am. Chem. Soc. 2007, 129, 12396.
20. Rajeswaran, W. G.; Cohen, L. A. Tetrahedron 1998, 54, 11375.
21. Huang, A.; Kodanko, J. J.; Overman, L. E. J. Am. Chem. Soc. 2004, 126, 14043.
22. Szabó-Pusztay, Z.; Szabó, L. Synthesis 1979, 276.
23. Kende, A. S.; Hodges, J. C. Synth. Commun. 1982, 12, 1.
24. Altman, R. A.; Hyde, A. M.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2008, 130, 9613.
25. (a) Staab, H. A. Angew. Chem., Int. Ed. Engl. 1962, 7, 350.
26. (b) Shone, R. L.; Deason, J. R.; Miyano, M. J. Org. Chem. 1986, 51, 268.
27. (c) Werner, T.; Barrett, A. G. M. J. Org. Chem. 2006, 71, 4302.
28. (d) Toullec, P. Y.; Bonaccorsi, C.; Mezzetti, A.; Togni, A.; Trost, B. M. Proc. Natl. Acad. Sci. 2004, 101, 5810.
29. (e) Trost, B. M.; Xu, J. J. Org. Chem. 2007, 72, 9372.
30. Nimitz, J. S.; Mosher, H. S. J. Org. Chem. 1981, 46, 211. Alternatively, imadazole carboxylates can be prepared by reaction of the corresponding alcohol and 1,1′-carbonyldiimidazole: see ref 14.
31. In the Supporting Information of ref 4a, Sodeoka reported two examples of the acylation of 3-(o-anisyl)oxindole in 42 and 70% yield. We thank one of the referees for alerting us to these two cases.
32. For a standard deprotection procedure of N-Moc-oxindole, see Supporting Information.