Asymmetric allylic alkylation of pyrroles and 4,7-dihydroindoles with alkene-phosphine ligands

Journal of Organic Chemistry

Volumn 77, Issue 9, 2012, Pages 4479-4483

  Liu, Yilin ^a   Cao, Ziping ^a   Du, Haifeng ^a  

^a INSTITUTE OF CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYLIC ALKYLATION; ASYMMETRIC ALLYLIC ALKYLATIONS; CATALYTIC SYSTEM; CHIRAL LIGAND; ENANTIOSELECTIVE; HIGH YIELD; HYBRID LIGAND; PALLADIUM-CATALYZED;

ALLYLATION; OLEFINS; PHOSPHORUS COMPOUNDS;

LIGANDS;

ALKENE; INDOLE DERIVATIVE; LIGAND; PALLADIUM; PHOSPHINE; PYRROLE;

ALKYLATION; ARTICLE; CHIRALITY; ENANTIOSELECTIVITY;

ALKENES; ALKYLATION; ALLYL COMPOUNDS; CATALYSIS; INDOLES; LIGANDS; MOLECULAR STRUCTURE; PHOSPHINES; PYRROLES; STEREOISOMERISM;

EID: 84860625087     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo300539y     Document Type: Article

References (46)

1. For a recent review, see: d'Ischia, M.; Napolitano, A.; Pezzella, A. In Comprehensive Heterocyclic Chemistry III: Pyrroles and their Benzo Derivatives: Applications; Katritzky, A. R., Ramsden, C. A., Scriven, E. F. V., Taylor, R. J. K., Eds.; Elsevier: Amsterdam, 2008; Vol. 3, pp 353-388.
2. Evans, D. A.; Fandrick, K. R.; Song, H.-J.; Scheidt, K. A.; Xu, R. J. Am. Chem. Soc. 2007, 129, 10029-10041
3. Sibi, M. P.; Coulomb, J.; Stanley, L. M. Angew. Chem., Int. Ed. 2008, 47, 9913-9915
4. Blay, G.; Fernández, I.; Monleón, A.; Pedro, J. R.; Vila, C. Org. Lett. 2009, 11, 441-444
5. Liu, H.; Lu, S.-F.; Xu, J.; Du, D.-M. Chem. Asian J. 2008, 3, 1111-1121
6. Singh, P. K.; Singh, V. K. Org. Lett. 2010, 12, 80-83
7. Huang, Y.; Tokunaga, E.; Suzuki, S.; Shiro, M.; Shibata, N. Org. Lett. 2010, 12, 1136-1138
8. Arai, T.; Awata, A.; Wasai, M.; Yokoyama, N.; Masu, H. J. Org. Chem. 2011, 76, 5450-5456
9. Aikawa, K.; Honda, K.; Mimura, S.; Mikami, K. Tetrahedron Lett. 2011, 52, 6682-6686
10. Li, G.; Rowland, G. B.; Rowland, E. B.; Antilla, J. C. Org. Lett. 2007, 9, 4065-4068
11. Sheng, Y.-F.; Gu, Q.; Zhang, A.-J.; You, S.-L. J. Org. Chem. 2009, 74, 6899-6901
12. Nakamura, S.; Sakurai, Y.; Nakashima, H.; Shibata, N.; Toru, T. Synlett 2009, 1639-1642
13. Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2001, 123, 4370-4371
14. Liang, X.; Fan, J.; Shi, F.; Su, W. Tetrahedron Lett. 2010, 51, 2505-2507
15. Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395-422
16. Trost, B. M.; Crawley, M. L. Chem. Rev. 2003, 103, 2921-2943
17. Lu, Z.; Ma, S. Angew. Chem., Int. Ed. 2008, 47, 258-297
18. Bandini, M.; Melloni, A.; Piccinelli, F.; Sinisi, R.; Tommasi, S.; Umani-Ronchi, A. J. Am. Chem. Soc. 2006, 128, 1424-1425
19. Zhuo, C.-X.; Liu, W.-B.; Wu, Q.-F.; You, S.-L. Chem. Sci. 2012, 3, 205-208
20. 2-catalyzed alkylation of pyrrole, see: Yuan, F.-Q.; Gao, L.-X.; Han, F.-S. Chem. Commun. 2011, 47, 5289-5291
21. Cao, Z.; Liu, Y.; Liu, Z.; Feng, X.; Zhuang, M.; Du, H. Org. Lett. 2011, 13, 2164-2167
22. Miyashita, A.; Yasuda, A.; Takaya, H.; Toriumi, K.; Ito, T.; Souchi, T.; Noyori, R. J. Am. Chem. Soc. 1980, 102, 7932-7934
23. Trost, B. M.; Van Vranken, D. L.; Bingel, C. J. Am. Chem. Soc. 1992, 114, 9327-9343
24. Uozumi, Y.; Hayashi, T. J. Am. Chem. Soc. 1991, 113, 9887-9888
25. Reiser, O. Angew. Chem., Int. Ed. Engl. 1993, 32, 547-549
26. von Matt, P.; Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 566-568
27. Glorius, F. Angew. Chem., Int. Ed. 2004, 43, 3364-3366
28. Defieber, C.; Grützmacher, H.; Carreira, E. M. Angew. Chem., Int. Ed. 2008, 47, 4482-4502
29. Shintani, R.; Hayashi, T. Aldrichim. Acta 2009, 42, 31-38
30. Tian, P.; Dong, H.-Q.; Lin, G.-Q. ACS Catal. 2012, 2, 95-119
31. Maire, P.; Deblon, S.; Breher, F.; Geier, J.; Böhler, C.; Rüegger, H.; Schönberg, H.; Grützmacher, H. Chem.-Eur. J. 2004, 10, 4198-4205
32. Shintani, R.; Duan, W.-L.; Nagano, T.; Okada, A.; Hayashi, T. Angew. Chem., Int. Ed. 2005, 44, 4611-4614
33. Defieber, C.; Ariger, M. A.; Moriel, P.; Carreira, E. M. Angew. Chem., Int. Ed. 2007, 46, 3139-3143
34. Minuth, T.; Boysen, M. M. K. Org. Lett. 2009, 11, 4212-4215
35. Liu, Z.; Du, H. Org. Lett. 2010, 12, 3054-3057
36. Cao, Z.; Liu, Z.; Liu, Y.; Du, H. J. Org. Chem. 2011, 76, 6401-6406
37. Yu, J.; Gaunt, M. J.; Spencer, J. B. J. Org. Chem. 2002, 67, 4627-4629
38. Dunne, J. P.; Aiken, S.; Duckett, S. B.; Konya, D.; Leñero, K. Q. A.; Drent, E. J. Am. Chem. Soc. 2004, 126, 16708-16709
39. Canovese, L.; Santo, C.; Visentin, F. Organometallics 2008, 27, 3577-3581
40. Çavdar, H.; Saraçoǧlu, N. Tetrahedron 2005, 61, 2401
41. Zeng, M.; Kang, Q.; He, Q.-L.; You, S.-L. Adv. Synth. Catal. 2008, 350, 2169-2173
42. Kang, Q.; Zheng, X.-J.; You, S.-L. Chem.-Eur. J. 2008, 14, 3539-3542
43. Hong, L.; Liu, C.; Sun, W.; Wang, L.; Wong, K.; Wang, R. Org. Lett. 2009, 11, 2177-2180
44. Sheng, Y.-F.; Li, G.-Q.; Kang, Q.; Zhang, A.-J.; You, S.-L. Chem.-Eur. J. 2009, 15, 3351-3354
45. Hong, L.; Sun, W.; Liu, C.; Wang, L.; Wong, K.; Wang, R. Chem.-Eur. J. 2009, 15, 11105-11108
46. Sakamoto, T.; Itoh, J.; Mori, K.; Akiyama, T. Org. Biomol. Chem. 2010, 8, 5448-5454