Enantioselective synthesis of planar chiral ferrocenes via Pd(0)-catalyzed intramolecular direct C-H bond arylation

Journal of the American Chemical Society

Volumn 136, Issue 13, 2014, Pages 4841-4844

  Gao, De Wei ^a   Yin, Qin ^a   Gu, Qing ^a   You, Shu Li ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUNDS; CATALYSIS; ORGANOMETALLICS;

AMINATION REACTION; ASYMMETRIC ALLYLIC ALKYLATIONS; CHIRAL FERROCENES; EFFICIENT SYNTHESIS; ENANTIOSELECTIVE; ENANTIOSELECTIVE SYNTHESIS; FERROCENE LIGANDS; MILD REACTION CONDITIONS;

ENANTIOSELECTIVITY;

FERROCENE DERIVATIVE; PALLADIUM; PLANAR CHIRAL FERROCENE; UNCLASSIFIED DRUG; ALLYL COMPOUND; FERROCENE; FERROUS ION;

AMINATION; ARTICLE; ARYLATION; ASYMMETRIC CATALYSIS; CHIRALITY; COLUMN CHROMATOGRAPHY; DIASTEREOISOMER; ENANTIOSELECTIVITY; STEREOCHEMISTRY; SYNTHESIS; ALKYLATION; CATALYSIS; CHEMISTRY; STEREOISOMERISM;

ALKYLATION; ALLYL COMPOUNDS; AMINATION; CATALYSIS; FERROUS COMPOUNDS; PALLADIUM; STEREOISOMERISM;

EID: 84897507841     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja500444v     Document Type: Article

References (76)

1. Hayashi, T., Togni, A., Eds. Ferrocenes; VCH: Weinheim, Germany, 1995.
2. Togni, A., Haltermann, R. L., Eds. Metallocenes; VCH: Weinheim, Germany, 1998.
3. Stepnicka, P., Ed. Ferrocenes; Wiley: Chichester, 2008.
4. Dai, L.-X., Hou, X.-L., Eds. Chiral Ferrocenes in Asymmetric Catalysis; Wiley: New York, 2010.
5. Halterman, R. L. Chem. Rev. 1992, 92, 965
6. Togni, A. Angew. Chem., Int. Ed. Engl. 1996, 35, 1475
7. Richards, C. J.; Locke, A. J. Tetrahedron: Asymmetry 1998, 9, 2377
8. Fu, G. C. Acc. Chem. Res. 2000, 33, 412
9. Dai, L.-X.; Tu, T.; You, S.-L.; Deng, W.-P.; Hou, X.-L. Acc. Chem. Res. 2003, 36, 659
10. Colacot, T. J. Chem. Rev. 2003, 103, 3101
11. Fu, G. C. Acc. Chem. Res. 2004, 37, 542
12. Arrayás, R. G.; Adrio, J.; Carretero, J. C. Angew. Chem., Int. Ed. 2006, 45, 7674
13. Fu, G. C. Acc. Chem. Res. 2006, 39, 853
14. Arae, S.; Ogasawara, M. J. Synth. Org. Chem. 2012, 70, 593
15. Schaarschmidt, D.; Lang, H. Organometallics 2013, 32, 5668
16. Siegel, S.; Schmalz, H.-G. Angew. Chem., Int. Ed. Engl. 1997, 36, 2456
17. Günay, M. E.; Richards, C. J. Organometallics 2009, 28, 5833
18. Dendele, N.; Bisaro, F.; Gaumont, A.-C.; Perrio, S.; Richards, C. J. Chem. Commun. 2012, 48, 1991
19. Takebayashi, S.; Shizuno, T.; Otani, T.; Shibata, T. Beilstein J. Org. Chem. 2012, 8, 1844
20. Takebayashi, S.; Shibata, T. Organometallics 2012, 31, 4114
21. Zhang, H.; Cui, X.; Yao, X.; Wang, H.; Zhang, J.; Wu, Y. Org. Lett. 2012, 14, 3012
22. Singh, K. S.; Dixneuf, P. H. Organometallics 2012, 31, 7320
23. Piotrowicz, M.; Zakrzewski, J. Organometallics 2013, 32, 5709
24. Battelle, L. F.; Bau, R.; Gokel, G. W.; Oyakawa, R. T.; Ugi, I. K. J. Am. Chem. Soc. 1973, 95, 482
25. Gokel, G. W.; Marquarding, D.; Ugi, I. K. J. Org. Chem. 1972, 37, 3052
26. Rebiere, F.; Riant, O.; Ricard, L.; Kagan, H. B. Angew. Chem., Int. Ed. Engl. 1993, 32, 568
27. Riant, O.; Samuel, O.; Kagan, H. B. J. Am. Chem. Soc. 1993, 115, 5835
28. Richards, C. J.; Damalidis, T.; Hibbs, D. E.; Hursthouse, M. B. Synlett 1995, 74
29. Riant, O.; Samuel, O.; Flessner, T.; Taudien, S.; Kagan, H. B. J. Org. Chem. 1997, 62, 6733
30. Enders, D.; Peters, R.; Lochtman, R.; Raabe, G. Angew. Chem., Int. Ed. 1999, 38, 2421
31. Bolm, C.; Kesselgruber, M.; Muñiz, K.; Raabe, G. Organometallics 2000, 19, 1648
32. Bolm, C.; Kesselgruber, M.; Raabe, G. Organometallics 2002, 21, 707
33. Tsukazaki, M.; Tinkl, M.; Roglans, A.; Chapell, B. J.; Taylor, N. J.; Snieckus, V. J. Am. Chem. Soc. 1996, 118, 685
34. Laufer, R. S.; Veith, U.; Taylor, N. J.; Snieckus, V. Org. Lett. 2000, 2, 629
35. Genet, C.; Canipa, S. J.; O'Brein, P.; Taylor, S. J. Am. Chem. Soc. 2006, 128, 9336
36. Alba, A.-N. R.; Rios, R. Molecules 2009, 14, 4747
37. Bueno, A.; Rosol, M.; Garcia, J.; Moyano, A. Adv. Synth. Catal. 2006, 348, 2590
38. Alba, A.-N.; Gomez-Sal, P.; Rios, R.; Moyano, A. Tetrahedron: Asymmetry 2009, 20, 1314
39. Ogasawara, M.; Watanabe, S.; Fan, L.; Nakajima, K.; Takahashi, T. Organometallics 2006, 25, 5201
40. Ogasawara, M.; Watanabe, S.; Nakajima, K.; Takahashi, T. Pure Appl. Chem. 2008, 80, 1109
41. Ogasawara, M.; Watanabe, S.; Nakajima, K.; Takahashi, T. J. Am. Chem. Soc. 2010, 132, 2136
42. Ogasawara, M.; Wu, W.-Y.; Arae, S.; Watanabe, S.; Morita, T.; Takahashi, T.; Kamikawa, K. Angew. Chem., Int. Ed. 2012, 51, 2951
43. Ogasawara, M.; Arae, S.; Watanabe, S.; Nakajima, K.; Takahashi, T. Chem. - Eur. J. 2013, 19, 4151
44. Ogasawara, M.; Watanabe, S. Synthesis 2009, 1761
45. Gao, D.-W.; Shi, Y.-C.; Gu, Q.; Zhao, Z.-L.; You, S.-L. J. Am. Chem. Soc. 2013, 135, 86
46. Shi, Y.-C.; Yang, R.-F.; Gao, D.-W.; You, S.-L. Beilstein J. Org. Chem. 2013, 9, 1891
47. Xia, J.-B.; You, S.-L. Organometallics 2007, 26, 4869
48. Giri, R.; Shi, B.-F.; Engle, K. M.; Maugel, N.; Yu, J.-Q. Chem. Soc. Rev. 2009, 38, 3242
49. Peng, H. M.; Dai, L.-X.; You, S.-L. Angew. Chem., Int. Ed. 2010, 49, 5826
50. Wencel-Delord, J.; Colobert, F. Chem. - Eur. J. 2013, 19, 14010
51. Engle, K. M.; Yu, J.-Q. J. Org. Chem. 2013, 78, 8927
52. Zheng, C.; You, S.-L. RSC Adv. 2014, 4, 6173
53. Mikami, K.; Hatano, M.; Terada, M. Chem. Lett. 1999, 28, 55
54. Kakiuchi, F.; Le Gendre, P.; Yamada, A.; Ohtaki, H.; Murai, S. Tetrahedron: Asymmetry 2000, 11, 2647
55. Thalji, R. K.; Ellman, J. A.; Bergman, R. G. J. Am. Chem. Soc. 2004, 126, 7192
56. Shi, B.-F.; Maugel, N.; Zhang, Y.-H.; Yu, J.-Q. Angew. Chem., Int. Ed. 2008, 47, 4882
57. Albicker, M. R.; Cramer, N. Angew. Chem., Int. Ed. 2009, 48, 9139
58. Shi, B.-F.; Zhang, Y.-H.; Lam, J. K.; Wang, D.-H.; Yu, J.-Q. J. Am. Chem. Soc. 2010, 132, 460
59. Renaudat, A.; Jean-Gérard, L.; Jazzar, R.; Kefalidis, C. E.; Clot, E.; Baudoin, O. Angew. Chem., Int. Ed. 2010, 49, 7261
60. Wasa, M.; Engle, K. M.; Lin, D. W.; Yoo, E. J.; Yu, J.-Q. J. Am. Chem. Soc. 2011, 133, 19598
61. Nakanishi, M.; Katayev, D.; Besnard, C.; Kündig, E. P. Angew. Chem., Int. Ed. 2011, 50, 7438
62. Anas, S.; Cordi, A.; Kagan, H. B. Chem. Commun. 2011, 47, 11483
63. Musaev, D. G.; Kaledin, A.; Shi, B.-F.; Yu, J.-Q. J. Am. Chem. Soc. 2012, 134, 1690
64. Katayev, D.; Nakanishi, M.; Bürgi, T.; Kündig, E. P. Chem. Sci. 2012, 3, 1422
65. Saget, T.; Lemouzy, S. J.; Cramer, N. Angew. Chem., Int. Ed. 2012, 51, 2238
66. Martin, N.; Pierre, C.; Davi, M.; Jazzar, R.; Baudoin, O. Chem. - Eur. J. 2012, 18, 4480
67. Yamaguchi, K.; Yamaguchi, J.; Studer, A.; Itami, K. Chem. Sci. 2012, 3, 2165
68. Shintani, R.; Otomo, H.; Ota, K.; Hayashi, T. J. Am. Chem. Soc. 2012, 134, 7305
69. Saget, T.; Cramer, N. Angew. Chem., Int. Ed. 2012, 51, 12842
70. Saget, T.; Cramer, N. Angew. Chem., Int. Ed. 2013, 52, 7865
71. Katayev, D.; Jia, Y.-X.; Sharma, A. K.; Banerjee, D.; Besnard, C.; Sunoj, R. B.; Kündig, E. P. Chem. - Eur. J. 2013, 19, 11916
72. Larionov, E.; Nakanishi, M.; Katayev, D.; Besnard, C.; Kündig, E. P. Chem. Sci. 2013, 4, 1995
73. Cheng, X.-F.; Li, Y.; Su, Y.-M.; Yin, F.; Wang, J.-Y.; Sheng, J.; Vora, H. U.; Wang, X.-S.; Yu, J.-Q. J. Am. Chem. Soc. 2013, 135, 1236
74. Chu, L.; Wang, X.-C.; Moore, C. E.; Rheingold, A. L.; Yu, J.-Q. J. Am. Chem. Soc. 2013, 135, 16344
75. Pi, C.; Li, Y.; Cui, X.; Zhang, H.; Han, Y.; Wu, Y. Chem. Sci. 2013, 4, 2675
76. Fukuzawa, S.-i.; Yamamoto, M.; Hosaka, M.; Kikuchi, S. Eur. J. Org. Chem. 2007, 5540