Enantioselective and regioselective indium(III)-catalyzed addition of pyrroles to isatins

Organic Letters

Volumn 13, Issue 21, 2011, Pages 5754-5757

  Gutierrez, Elisa G ^a   Wong, Casey J ^a   Sahin, Aziza H ^a   Franz, Annaliese K ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

INDIUM; ISATIN; PYRROLE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

CATALYSIS; INDIUM; ISATIN; MOLECULAR STRUCTURE; PYRROLES; STEREOISOMERISM;

EID: 80055097274     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol202329s     Document Type: Article

References (32)

1. Kagata, T.; Saito, S.; Shigemori, H.; Ohsaki, A.; Kubota, H.; Kobayashi, J. J. Nat. Prod. 2006, 69, 1517
2. Tokunaga, T.; Hume, W. E.; Nagamine, J.; Kawamura, T.; Taiji, M.; Nagata, R. Bioorg. Med. Chem. Lett. 2005, 15, 1789
3. Koguchi, Y.; Kohno, J.; Nishio, M.; Takahashi, K.; Okuda, T.; Ohnuki, T.; Komatsubara, S. J. Antibiot. 2000, 53, 105
4. Zhang, H. P.; Kamano, Y.; Ichihara, Y.; Kizu, H.; Komiyama, K.; Itokawa, H.; Pettit, G. R. Tetrahedron 1995, 51, 5523
5. Yong, S. R.; Ung, A. T.; Pyne, S. G.; Skelton, B. W.; White, A. H. Tetrahedron 2007, 63, 5579
6. Itoh, T.; Ishikawa, H.; Hayashi, Y. Org. Lett. 2009, 11, 3854
7. Badillo, J. J.; Hanhan, N. V.; Franz, A. K. Curr. Opin. Drug Disc. 2010, 13, 758
8. Zhou, F.; Liu, Y.-L.; Zhou, J. Adv. Synth. Catal. 2010, 352, 1381
9. Zheng, K.; Yin, C.; Liu, X.; Lin, L.; Feng, X. Angew. Chem., Int. Ed. 2011, 50, 2573
10. Liu, L.; Zhang, S.-L.; Xue, F.; Lou, G.-S.; Zhang, H.-Y.; Ma, S.-C.; Duan, W.-H.; Wang, W. Chem. Eur. J 2011, 17, 7791
11. Hanhan, N. V.; Sahin, A. H.; Chang, T. W.; Fettinger, J. C.; Franz, A. K. Angew. Chem., Int. Ed. 2010, 49, 744
12. Evans, D. A.; K. R. F.; Song, H.; Scheidt, K. A.; Xu, R. J. Am. Chem. Soc. 2007, 129, 10029
13. Hargaden, G. C.; Guiry, P. J. Chem. Rev. 2009, 109, 2505
14. In this study, the (S,R)-indapybox ligand was synthesized using a modified procedure; see the Supporting Information and: Desimoni, G.; Faita, G.; Guala, M.; Pratelli, C. Tetrahedron: Asymmetry 2002, 13, 1651
15. For a recent review of indium in organic synthesis, see: Yadav, J. S.; Antony, A.; George, J.; Subba Reddy, B. V. Eur. J. Org. Chem. 2010, 591
16. Zhao, J.-F.; Tsui, H.-Y.; Wu, P.-J.; Lu, J.; Loh, T.-P. J. Am. Chem. Soc. 2008, 130, 16492
17. Zhao, J.-F.; Tan, B.-H.; Loh, T.-P. Chem. Sci. 2011, 2, 349
18. Chua, S.-S.; Alni, A.; Chan, L.-T. J.; Yamane, M.; Loh, T.-P. Tetrahedron 2011, 67, 5079
19. Hayashi, R.; Cook, G. R. Org. Lett. 2007, 9, 1311
20. Giera, D. S.; Schneider, C. Org. Lett. 2010, 12, 4884
21. For information on pyrrole polymer formation, see: Can, M.; Özaslan, H.; Ildak, Ö.; Pekmez, N. Ö.; Yildiz, A. Polymer 2004, 45, 7011
22. For information on pyrrole regioisomers, see: Voldhardt, P.; Schore, N. Organic Chemistry: Structure and Function; W. H. Freeman and Co.: New York, 2011.
23. For relative pyrrole reactivities, see: Nigst, T. A.; Westermaier, M.; Ofial, A. R.; Mayr, H. Eur. J. Org. Chem. 2008, 2369
24. Yadav, J. S.; Reddy, B. V. S.; Abraham, S.; Sabitha, G. Tetrahedron Lett. 2002, 43, 1565
25. Huang, Y.; Suzuki, S.; Shiro, M.; Shibata, N. Org. Lett. 2010, 12, 1136
26. Singh, P. K.; Singh, V. K. S. Org. Lett. 2010, 12, 80
27. Yadav, J. S.; SubbaReddy, B. V.; Gayathri, K. U.; Meraj, S.; Prasad, A. R. Synthesis 2006, 4121
28. Zhao, J.-F.; Tjan, T.-B. W.; Loh, T.-P. Tetrahedron Lett. 2010, 51, 5649
29. Zhao, J.-F.; Tjan, T.-B. W.; Tan, B.-H.; Loh, T.-P. Org. Lett. 2009, 11, 5714
30. While investigating various additives, it was discovered that the use and efficient activation of 4 Å molecular sieves was critical for optimal catalyst performance, affording faster and more efficient conversion. Further investigation into the role of molecular sieves in this reaction is required. See: Posner, G. H.; Dai, H.; Bull, D. S.; Lee, J.; Eydoux, F.; Ishihara, Y.; Welsh, W.; Pryor, N.; Petr, S. J. Org. Chem. 1996, 61, 671
31. Britovsek, G. J. P.; England, J.; Spitzmesser, S. K.; White, A. J. P.; Williams, D. J. Dalton Trans. 2005, 945
32. Paira, P.; Hazra, A.; Kumar, S.; Paira, R.; Sahu, K. B.; Naskar, S.; Saha, P.; Mondal, S.; Maity, A.; Banerjee, S.; Mondal, N. B. Bioorg. Med. Chem. Lett. 2005, 15, 1789