Cationic palladium complex-catalyzed diastereoselective tandem annulation of 2-iminoarylboronic acids with substituted alkynes: Enantioselective synthesis of aminoindene derivatives by double asymmetric induction

Advanced Synthesis and Catalysis

Volumn 353, Issue 14-15, 2011, Pages 2805-2813

  Yu, Xufen ^a   Lu, Xiyan ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

alkynes; aminoindenes; boronic acids; cationic palladium complexes; double asymmetric induction

Indexed keywords

EID: 80054769988     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201100363     Document Type: Article

References (71)

1. U. Akbulut, A. Khurshid, B. Hacioǧlu, L. Toppare, Polymer 1990, 31, 1343
2. J. Barberá, O. A. Rakitin, M. B. Ros, T. Torroba, Angew. Chem. 1998, 110, 308
3. Angew. Chem. Int. Ed. 1998, 37, 296
4. J. Yang, M. V. Lakshmikantham, M. P. Cava, D. Lorcy, J. R. Bethelot, J. Org. Chem. 2000, 65, 6739.
5. A. Korte, J. Legros, C. Bolm, Synlett 2004, 2397 and references cited therein.
6. R. B. Miller, J. M. Frincke, J. Org. Chem. 1980, 45, 5312.
7. V. Cadierno, J. Díez, G. M. P. Gamasa, J. Gimeno, E. Lastra, Coord. Chem. Rev. 1999, 193-195, 147
8. D. Zargarian, Coord. Chem. Rev. 2002, 233-234, 157
9. R. Leino, P. Lehmus, A. Lehtonen, Eur. J. Inorg. Chem. 2004, 3201.
10. M. F. Semmelhack, S. Ho, D. Cohen, M. Steigerwald, M. C. Lee, G. Lee, A. M. Gilbert, W. D. Wulff, R. G. Ball, J. Am. Chem. Soc. 1994, 116, 7108
11. R. L. Halterman, C. Zhu, Tetrahedron Lett. 1999, 40, 7445
12. K. R. Romines, K. D. Lovasz, S. A. Mizsak, J. K. Morris, E. P. Seest, F. Han, J. Tulinsky, T. M. Judge, R. B. Gammill, J. Org. Chem. 1999, 64, 1733
13. Z. Xi, R. Guo, S. Mito, H. Yan, K. Kanno, K. Nakajima, T. Takahashi, J. Org. Chem. 2003, 68, 1252
14. L.-M. Yuan, R. J. Madhushaw, R.-S. Liu, J. Org. Chem. 2004, 69, 7700
15. K.-J. Chang, D. K. Rayabarapu, C.-H. Cheng, J. Org. Chem. 2004, 69, 4781
16. M. Lautens, T. Marquardt, J. Org. Chem. 2004, 69, 4607.
17. Y. Ishiguro, K. Okamoto, F. Ojima, Y. Sonoda, Chem. Lett. 1993, 1139
18. J. Vicente, J.-A. Abad, J. Gil-Rubio, Organometallics 1996, 15, 3509
19. L. G. Quan, V. Gevorgyan, Y. Yamamoto, J. Am. Chem. Soc. 1999, 121, 3545
20. R. C. Larock, M. J. Doty, S. Cacchi, J. Org. Chem. 1993, 58, 4579
21. A. A. Pletnev, Q. Tian, R. C. Larock, J. Org. Chem. 2002, 67, 9276
22. D. K. Rayabarapu, C.-H. Yang, C.-H. Cheng, J. Org. Chem. 2003, 68, 6726
23. T. Matsuda, M. Makino, M. Murakami, Chem. Lett. 1993, 1416.
24. H. Tsukamoto, T. Ueno, Y. Kondo, Org. Lett. 2007, 9, 3033
25. C.-C. Liu, R. P. Korivi, C.-H. Cheng, Chem. Eur. J. 2008, 14, 9503.
26. Y. Kuninobu, A. Kawata, K. Takai, J. Am. Chem. Soc. 2005, 127, 13498
27. Y. Kuninobu, Y. Tokunaga, A. Kawata, K. Takai, J. Am. Chem. Soc. 2006, 128, 202
28. Y. Kuninobu, Y. Nishina, M. Shouho, K. Takai, Angew. Chem. 2006, 118, 2832
29. Angew. Chem. Int. Ed. 2006, 45, 2766
30. Y. Kuninobu, Y. Nishina, K. Okaguchi, M. Shouho, K. Takai, Bull. Chem. Soc. Jpn. 2008, 81, 1393.
31. Z.-M. Sun, S.-P. Chen, P. Zhao, Chem. Eur. J. 2010, 16, 2619.
32. For reactions catalyzed by rhodium species, see: M. Ueda, N. Miyaura, J. Organomet. Chem. 2000, 595, 31
33. J. R. Porter, J. F. Traverse, A. H. Hoveyda, M. L. Snapper, J. Am. Chem. Soc. 2001, 123, 10409
34. N. Hermanns, S. Dahmen, C. Bolm, S. Bräse, Angew. Chem. 2002, 114, 3844
35. Angew. Chem. Int. Ed. 2002, 41, 3692
36. A. A. Boezio, J. Pytkowicz, A. Côte, A. B. Charette, J. Am. Chem. Soc. 2003, 125, 14260
37. N. Tokunaga, Y. Otomaru, K. Okamoto, K. Ueyama, R. Shintani, T. Hayashi, J. Am. Chem. Soc. 2004, 126, 13584
38. M. Kuriyama, T. Soeta, X. Hao, Q. Chen, K. Tomioka, J. Am. Chem. Soc. 2004, 126, 8128
39. D. J. Weix, Y. Shi, J. A. Ellman, J. Am. Chem. Soc. 2005, 127, 1092
40. R. B. C. Jagt, P. Y. Toullec, D. Geerdink, J. G. Devries, B. L. Feringa, A. J. Minnaard, Angew. Chem. 2006, 118, 2855
41. Angew. Chem. Int. Ed. 2006, 45, 2789
42. Z.-Q. Wang, C.-G. Feng, M.-H. Xu, G.-Q. Lin, J. Am. Chem. Soc. 2007, 129, 5336. For reactions catalyzed by palladium species, see
43. H. Dai, X. Lu, Org. Lett. 2007, 9, 3077
44. P. He, Y. Lu, Q. S. Hu, Tetrehedron Lett. 2007, 48, 5283.
45. J. Tsuji, (Ed.), Palladium Reagent and Catalysis: Innovations in Organic Synthesis, John, Wiley: Chichester, U.K., 1995
46. B. C. Soderberg, in: Comprehensive Organometallic Chemistry II, Vol. 12, (Eds.:, E. W. Abel, F. G. A. Stone, G. Wilkinson,), Pergamon, Oxford, 1995, p 241.
47. For reviews, see: N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457
48. K. Soai, T. Shibata, in: Comprehensive Asymmetric Catalysis, (Eds.:, E. N. Jacobsen, A. Pfaltz, H. Yamamoto,), Springer Verlag, Berlin, 2004, Suppl. 1, pp 95-106
49. D. G. Hall, (Ed.), Boronic Acids: Preparation and Applications in Organic Synthesis and Medicine, Wiley-VCH, Weinheim, Germany, 2005.
50. G. Liu, X. Lu, J. Am. Chem. Soc. 2006, 128, 16504
51. B. Zhao, X. Lu, Tetrahedron Lett. 2006, 47, 6765
52. B. Zhao, X. Lu, Org. Lett. 2006, 8, 5987
53. J. Song, Q. Shen, F. Xu, X. Lu, Org. Lett. 2007, 9, 2947
54. G. Liu, X. Lu, Adv. Synth. Catal. 2007, 349, 2247
55. M. Yang, X. Zhang, X. Lu, Org. Lett. 2007, 9, 5131
56. X. Yu, X. Lu, Org. Lett. 2009, 11, 4366
57. X. Han, X. Lu, Org. Lett. 2010, 12, 108.
58. M. T. Robak, M. A. Herbage, J. A. Ellman, Chem. Rev. 2010, 110, 3600.
59. J. A. Ellman, T. D. Owens, T. P. Tang, Acc. Chem. Res. 2002, 35, 984
60. J. A. Ellman, Pure Appl. Chem. 2003, 75, 39
61. F. Ferreira, C. Botuha, F. Chemla, A. Pérez-Luna, Chem. Soc. Rev. 2009, 38, 1162.
62. G.-Q. Lin, M.-H. Xu, Y.-W. Zhong, X.-W. Sun, Acc. Chem. Res. 2008, 41, 831
63. D. Morton, R. A. Stockman, Tetrahedron 2006, 62, 8869.
64. See Supporting Information. Crystallographic data for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Center as supplementary publications CCDC 813304 (7aa) and CCDC 813305 (7aa′). These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via or on application to CCDC, 12 Union Road, Cambridge CB21EZ, UK (fax: +44-1223-336-033; e-mail: deposit@ccdc.cam.ac.uk).: M. Terada, N. Sayo, K. Mikami, Synlett 1995, 411.
65. M. A. Beenen, D. J. Weix, J. A. Ellman, J. Am. Chem. Soc. 2006, 128, 6304
66. J. A. Smulik, E. Vedejs, Org. Lett. 2003, 5, 4187.
67. J. L. G. Ruano, J. Alemán, M. B. Cid, A. Parra, Org. Lett. 2005, 7, 179
68. J. L. G. Ruano, J. Alemán, A. Parra, M. B. Cid, Org. Synth. 2007, 84, 129.
69. C. Pisano, G. Consigilio, A. Sironi, M. Moret, J. Chem. Soc. Chem. Commun. 1991, 421
70. T. Nishikata, Y. Yamamoto, N. Miyaura, Organometallics 2004, 23, 4317, and references cited therein
71. P. J. Stang, D. H. Cao, G. T. Poulter, A. M. Arif, Organometallics 1995, 14, 1110.