Intramolecular dearomatizing [3 + 2] annulation of α-imino carbenoids with aryl rings furnishing 3,4-fused indole skeletons

Journal of the American Chemical Society

Volumn 136, Issue 6, 2014, Pages 2272-2275

  Miura, Tomoya ^a   Funakoshi, Yuuta ^a   Murakami, Masahiro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CYCLIZATION; INDOLES; METHANE; MOLECULAR STRUCTURE; RHODIUM;

EID: 84894115779     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja412663a     Document Type: Article

References (57)

1. Peat, A. J.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 1028
2. Stoffman, E. J. L.; Clive, D. L. J. Tetrahedron 2010, 66, 4452
3. Kato, K.; Ono, M.; Akita, H. Tetrahedron 2001, 57, 10055
4. Xu, X.-B.; Liu, J.; Zhang, J.-J.; Wang, Y.-W.; Peng, Y. Org. Lett. 2013, 15, 550
5. Baran, P. S.; Maimone, T. J.; Richter, J. M. Nature 2007, 446, 404
6. Rafferty, R. J.; Williams, R. M. J. Org. Chem. 2012, 77, 519
7. Allan, K. M.; Kobayashi, K.; Rawal, V. H. J. Am. Chem. Soc. 2012, 134, 1392
8. Quasdorf, K. W.; Huters, A. D.; Lodewyk, M. W.; Tantillo, D. J.; Garg, N. K. J. Am. Chem. Soc. 2012, 134, 1396
9. Wood, J. L. Nat. Chem. 2012, 4, 341
10. Ergot Alkaloids and Related Compounds. Handbook of Experimental Pharmacology; Berde, B.; Schild, H. O., Eds.; Springer-Verlag: Berlin, 1978; Vol. 49.
11. Umezaki, S.; Yokoshima, S.; Fukuyama, T. Org. Lett. 2013, 15, 4230
12. Liu, Q.; Zhang, Y.-A.; Xu, P.; Jia, Y. J. Org. Chem. 2013, 78, 10885
13. Yokoyama, Y.; Kondo, K.; Mitsuhashi, M.; Murakami, Y. Tetrahedron Lett. 1996, 37, 9309
14. Yamada, F.; Makita, Y.; Somei, M. Heterocycles 2007, 72, 599
15. Liras, S.; Lynch, C. L.; Fryer, A. M.; Vu, B. T.; Martin, S. F. J. Am. Chem. Soc. 2001, 123, 5918
16. Zhang, Y.-A.; Iiu, Q.; Wang, C.; Jia, Y. Org. Lett. 2013, 15, 3662
17. Greshock, T. J.; Funk, R. L. J. Am. Chem. Soc. 2006, 128, 4946
18. Park, I.-K.; Park, J.; Cho, C.-G. Angew. Chem., Int. Ed. 2012, 51, 2496
19. Breazzano, S. P.; Poudel, Y. B.; Boger, D. L. J. Am. Chem. Soc. 2013, 135, 1600
20. Shan, D.; Gao, Y.; Jia, Y. Angew. Chem., Int. Ed. 2013, 52, 4902 and references therein
21. García-Fortanet, J.; Kessler, F.; Buchwald, S. L. J. Am. Chem. Soc. 2009, 131, 6676
22. Leon, R.; Jawalekar, A.; Redert, T.; Gaunt, M. J. Chem. Sci. 2011, 2, 1487
23. Phipps, R. J.; Toste, F. D. J. Am. Chem. Soc. 2013, 135, 1268
24. Zhuo, C.-X.; You, S.-L. Angew. Chem., Int. Ed. 2013, 52, 10056 and references therein
25. Horneff, T.; Chuprakov, S.; Chernyak, N.; Gevorgyan, V.; Fokin, V. V. J. Am. Chem. Soc. 2008, 130, 14972
26. Miura, T.; Yamauchi, M.; Murakami, M. Chem. Commun. 2009, 1470
27. Chuprakov, S.; Hwang, F. W.; Gevorgyan, V. Angew. Chem., Int. Ed. 2007, 46, 4757
28. Alford, J. S.; Spangler, J. E.; Davies, H. M. L. J. Am. Chem. Soc. 2013, 135, 11712
29. Miura, T.; Tanaka, T.; Yada, A.; Murakami, M. Chem. Lett. 2013, 42, 1308
30. Parr, B. T.; Davies, H. M. L. Angew. Chem., Int. Ed. 2013, 52, 10044
31. Chattopadhyay, B.; Gevorgyan, V. Angew. Chem., Int. Ed. 2012, 51, 862
32. Gulevich, A. V.; Gevorgyan, V. Angew. Chem., Int. Ed. 2013, 52, 1371
33. Chattopadhyay, B.; Gevorgyan, V. Org. Lett. 2011, 13, 3746
34. Shi, Y.; Gevorgyan, V. Org. Lett. 2013, 15, 5394
35. Schultz, E. E.; Sarpong, R. J. Am. Chem. Soc. 2013, 135, 4696
36. Miura, T.; Hiraga, K.; Biyajima, T.; Nakamuro, T.; Murakami, M. Org. Lett. 2013, 15, 3298
37. Zibinsky, M.; Fokin, V. V. Angew. Chem., Int. Ed. 2013, 52, 1507
38. Chuprakov, S.; Kwok, S. W.; Fokin, V. V. J. Am. Chem. Soc. 2013, 135, 4652
39. Parr, B. T.; Green, S. A.; Davies, H. M. L. J. Am. Chem. Soc. 2013, 135, 4716
40. Spangler, J. E.; Davies, H. M. L. J. Am. Chem. Soc. 2013, 135, 6802
41. Miura, T.; Tanaka, T.; Hiraga, K.; Stewart, S. G.; Murakami, M. J. Am. Chem. Soc. 2013, 135, 13652
42. Danion, D.; Arnold, B.; Regitz, M. Angew. Chem., Int. Ed. Engl. 1981, 20, 113
43. Acheson, R. M.; Vernon, J. M. J. Chem. Soc. 1962, 1148
44. Lee, C. K.; Hahn, C. S.; Noland, W. E. J. Org. Chem. 1978, 43, 3727
45. Sheppard, G. S.; Vollhardt, K. P. C. J. Org. Chem. 1986, 51, 5496
46. Tanaka, K.; Yukimura, N.; Narasaka, K. Bull. Chem. Soc. Jpn. 2004, 77, 575
47. Raushel, J.; Fokin, V. V. Org. Lett. 2010, 12, 4952
48. McKervey, M. A.; Tuladhar, S. M.; Twohig, M. F. J. Chem. Soc., Chem. Commun. 1984, 129
49. Crombie, A. L.; Kane, J. L., Jr.; Shea, K. M.; Danheiser, R. L. J. Org. Chem. 2004, 69, 8652
50. Panne, P.; Fox, J. M. J. Am. Chem. Soc. 2007, 129, 22
51. Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds; John Wiley & Sons: New York, 1998; pp 289-324.
52. Danishefsky, S.; Cunningham, R. J. Org. Chem. 1965, 30, 3676
53. Uhle, F. C. J. Am. Chem. Soc. 1949, 71, 761
54. Teranishi, K.; Hayashi, S.; Nakatsuka, S.; Goto, T. Synthesis 1995, 506
55. Padwa, A.; Bur, S. K.; Zhang, H. J. Org. Chem. 2005, 70, 6833
56. MacKay, J. A.; Bishop, R. L.; Rawal, V. H. Org. Lett. 2005, 7, 3421
57. Yamawaki, M.; Tsutsui, H.; Kitagaki, S.; Anada, M.; Hashimoto, S. Tetrahedron Lett. 2002, 43, 9561 Technology Technology Technology Technology