Palladium-NHC catalyzed enantioselective synthesis of fused indolines via inert C(sp3)-H activation

Chimia

Volumn 66, Issue 4, 2012, Pages 241-243

  Nakanishi, Masafumi ^a   Katayev, Dmitry ^a   Besnard, Céline ^a   Kündig, E Peter ^a  

^a UNIVERSITY OF GENEVA   (Switzerland)

Author keywords

Asymmetric catalysis; C H Activation; Chiral NHC; Indoline; Palladium

Indexed keywords

EID: 84860732963     PISSN: 00094293     EISSN: None     Source Type: Journal    
DOI: 10.2533/chimia.2012.241     Document Type: Conference Paper

References (57)

1. X.-F. Wu, P. Anbarasan, H. Neumann, M. Beller, Angew. Chem. Int. Ed. 2010, 49, 9047.
2. Reviews: a) A. E. Chilov, G. B. Shul'pin, Chem. Rev. 1997, 97, 2879;
3. b) G. Dyker, Angew. Chem. Int. Ed. 1999, 38, 1699;
4. c) C. Jia, T. Kitamura, Y. Fujiwara, Acc. Chem. Res. 2001, 34, 633;
5. d) J. A. Labinger, J. E. Bercaw, Nature 2002, 417, 507;
6. e) V. Ritleng, C. Sirlin, M. Pfeffer, Chem. Rev. 2002, 102, 1731;
7. f) R. H. Crabtree, J. Organomet. Chem. 2004, 689, 4083;
8. g) K. Godula, D. Sames, D. Science 2006, 312, 67;
9. h) A. R. Dick, M. S. Sanford, Tetrahedron 2006, 62, 2439;
10. i) R. G. Bergman, R. G. Nature 2007, 446, 391;
11. j) D. A. Colby, R. G. Bergman, J. A. Ellman, Chem. Rev. 2010, 110, 624;
12. k) T. W. Lyons, M. S. Sanford, Chem. Rev. 2010, 110, 1147;
13. l) T. Newhouse, P. S. Baran, Angew. Chem. Int. Ed. 2011, 50, 3362;
14. Recent report: m) L. Huang, T. Niu, J. Wu, Y. Zhang, J. Org. Chem. 2011, 76, 1759.
15. Inert C(sp3)-H activation, see: a) H. Chen, S. Schlecht, T. C. Semple, J. F. Hartwig, Science 2000, 287, 1995;
16. b) O. Baudoin, A. Herrbach, F. Guéritte, Angew. Chem. Int. Ed. 2003, 42, 5736;
17. c) T. E. Barder, S. D. Walker, J. R. Martinelli, S. L. Buchwald, J. Am. Chem. Soc. 2005, 127, 4685;
18. d) R. Giri, N. Maugel, J.-J. Li, D.-H. Wang, S. P. Breazzano, L. B. Saunders, J.-Q. Yu, J. Am. Chem. Soc. 2007, 129, 3510;
19. e) M. Lafrance, S. I. Gorelsky, K. Fagnou, J. Am. Chem. Soc. 2007, 129, 14570;
20. f) S. Rousseaux, S. I. Gorelsky, B. K. W. Chung, K. Fagnou, J. Am. Chem. Soc. 2010, 132, 10692;
21. g) R. Jazzar, J. Hitce, A. Renaudat, J. Sofack-Kreutzer, O. Baudoin, Chem. Eur. J. 2010, 16, 2654;
22. h) J. H. Hansen, T. M. Gregg, S. R. Ovalles, Y. Lian, J. Autschbach, H. M. L. Davies, J. Am. Chem. Soc. 2011, 133, 5076;
23. i) K. M. Engle, T.-S. Mei, X. Wang, J.-Q. Yu, Angew. Chem. Int. Ed. 2011, 50, 1478 and refs cited therein.
24. a) M. Nakanishi, D. Katayev, C. Besnard, E. P. Kündig, Angew. Chem. Int. Ed. 2011, 50, 7438;
25. b) B.-F. Shi, N. Maugel, Y.-H. Zhang, J.-Q. Yu, Angew. Chem. Int. Ed. 2008, 47, 4882;
26. c) A. Renaudat, L. Jean-Gérad, R. Jazzar, C. E. Kefalidis, E. Clot, O. Baudoin, Angew. Chem. Int. Ed. 2010, 49, 7261;
27. d) S. Anas, A. Cordi, H. B. Kagan, Chem. Commun. 2011, 47, 11483;
28. e) S. Pan, K. Endo, T. Shibata, Org. Lett. 2011, 13, 4692;
29. f) T. Saget, S. J. Lemouzy, N. Cramer, Angew. Chem. Int. Ed. 2012, 51, 2238..
30. a) Review of Pd-catalyzed indole synthesis, see; S. Cacchi, G. Fabrizi, Chem. Rev. 2005, 105, 2873;
31. b) S. Cacchi, G. Fabrizi, Chem. Rev. 2011, 111, PR 215;
32. c) J. Barluennga, C. Valadés, in 'Modern Heterocyclic Chemistry', Vol. 1, Eds J. Alvarez-Builla, J. J. Vaquero, J. Barluenga, Wiley-VCH, Weinheim, 2011, p. 377-531.
33. Selected recent examples of the synthesis of fused indoline containing natural products: a) A. Huang, J. J. Kodanko, L. E. Overman, J. Am. Chem. Soc. 2004, 126, 14043;
34. b) Y. Kaburagi, H. Tokuyama, T. Fukuyama, J. Am. Chem. Soc. 2004, 126, 10246;
35. c) T. Kawasaki, M. Shinada, D. Kamimura, M. Ohzono, A. Ogawa, Chem. Commun. 2006, 420;
36. d) J. Yang, H. Wu, L. Shen, Y. Qin, J. Am. Chem. Soc. 2007, 129, 13794;
37. e) S. Jaegli, J.-P. Vors, L. Neuville, J. Zhu, Synlett 2009, 2997;
38. f) D. Kato, Y. Sasaki, D. L. Boger, J. Am. Chem. Soc. 2010, 132, 3685;
39. g) Z. Zuo, W. Xie, D. W. Ma, J. Am. Chem. Soc. 2010, 132, 13226;
40. h) D. Kato, Y. Sasaki, D. L. Boger, J. Am. Chem. Soc. 2010, 132, 3685;
41. i) V. J. Reddy, C. J. Douglas, Org. Lett. 2010, 12, 952.
42. Reviews: a) S. Anas, H. B. Kagan, Tetrahedron: Asymmetry 2009, 20, 2193;
43. b) D. Liu, G. Zhao, L. Xiang, Eur. J. Org. Chem. 2010, 3975;
44. c) Y.-J. Wu, 'Heterocyclic Scaffolds II: Topics in Heterocyclic Chemistry', Vol. 26, Ed. G. W. Gribble, Springer, Heidelberg, 2010.
45. a) T. Watanabe, S. Oishi, N. Fujii, H. Ohno, Org. Lett. 2008, 10, 1759;
46. b) J. J. Neumann, S. Rakshit, T. Dröge, F. Glorius, Angew. Chem. Int. Ed. 2009, 48, 6892;
47. c) S. Rousseaux, M. Davi, J. Sofack-Kreuzer, C. Pierre, C. E. Kefalidis, E. Clot, K. Fagnou, O. Baudoin, J. Am. Chem. Soc. 2010, 132, 10706;
48. For reports of highly enantioenriched cis-fused indolines see: a) F. O. Arp, G. C. Fu, J. Am. Chem. Soc. 2006, 128, 14264;
49. b) D.-S. Wang, Q.-A. Cheng, W. Li, C.-B. Yu, Y.-G. Zhou, X. Zhang, J. Am. Chem. Soc. 2010, 132, 8909.
50. G. Bernardinelli, D. Fernandez, R. Gosmini, P. Meier, A. Ripa, P. Schüpfer, B. Treptow, E. P. Kündig, Chirality, 2000, 12, 529.
51. a) E. P. Kündig, T. M. Seidel, Y.-X. Jia, G. Bernardinelli, Angew. Chem. Int. Ed. 2007, 46, 8484;
52. b) Y.-X. Jia, J. M. Hillgren, E. L. Watson, S. P. Marsden, E. P. Kündig, Chem. Commun. 2008, 4040;
53. c) Y.-X. Jia, D. Katayev, T. M. Seidel, G. Bernardinelli, E. P. Kündig, Chem. Eur. J. 2010, 16, 6300.
54. a) M. S. Viciu, R. F. Germaneau, O. Navarro- Fernandez, E. D. Stevens, S. P. Nolan, Organometallics 2002, 21, 5470;
55. b) N. Marion, O. Navarro, J. Mei, E. D. Stevens, N. M. Scott, S. P. Nolan, J. Am. Chem. Soc. 2006, 128, 4101.
56. M. Lafrance, K. Fagnou, J. Am. Chem. Soc. 2006, 128, 16496;
57. b) M. Lafrance, S. I. Gorelsky, K. Fagnou, J. Am. Chem. Soc. 2007, 129, 14570.