Dearomatization strategy of β-enamino ester: Construction of indenoazepines via tandem Michael addition/polycyclization

Organic Letters

Volumn 15, Issue 13, 2013, Pages 3464-3467

  Yang, Min ^a   Tang, Jie ^a   Fan, Renhua ^b  

^a EAST CHINA NORMAL UNIVERSITY   (China)

^b FUDAN UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

AZEPINE DERIVATIVE; ESTER; INDENE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; OXIDATION REDUCTION REACTION; STEREOISOMERISM; SYNTHESIS;

AZEPINES; CATALYSIS; CYCLIZATION; ESTERS; INDENES; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; STEREOISOMERISM;

EID: 84880002007     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol401553n     Document Type: Article

References (61)

1. Bach, T. Angew. Chem., Int. Ed. Engl. 1996, 35, 729
2. Quideau, S.; Pouységu, L. Org. Prep. Proced. Int. 1999, 31, 617
3. Pape, A. R.; Kaliappan, K. P.; Kündig, E. P. Chem. Rev. 2000, 100, 2917
4. Magdziak, D.; Meek, S. J.; Pettus, T. R. R. Chem. Rev. 2004, 104, 1383
5. Keane, J. M.; Harman, W. D. Organometallics 2005, 24, 1786
6. López Ortiz, F.; Iglesias, M. J.; Fernández, I.; Andújar Sánchez, C. M.; Gómez, G. R. Chem. Rev. 2007, 107, 1580
7. Quideau, S.; Pouységu, L.; Deffieux, D. Synlett 2008, 467
8. Pouységu, L.; Deffieux, D.; Quideau, S. Tetrahedron 2010, 66, 2235
9. Roche, S. P.; Porco, J. A., Jr. Angew. Chem., Int. Ed. 2011, 50, 4068
10. Zhuo, C.-X.; Zhang, W.; You, S.-L. Angew. Chem., Int. Ed. 2012, 51, 12662
11. Ding, Q.; Ye, Y.; Fan, R. Synthesis 2013, 45, 1
12. Biggs, T. N.; Swenton, J. S. J. Am. Chem. Soc. 1993, 115, 10416
13. Swenton, J. S.; Biggs, T. N.; Clark, W. M. J. Org. Chem. 1993, 58, 5607
14. Engler, T. A.; Wanner, J. J. Org. Chem. 2000, 65, 2444
15. Nicolaou, K. C.; Sugita, K.; Baran, P. S.; Zhong, Y.-L. Angew. Chem., Int. Ed. 2001, 40, 207
16. Parker, K. A.; Mindt, T. L. Org. Lett. 2002, 4, 4265
17. Nair, V.; Rajesh, C.; Vinod, A. U.; Bindu, S.; Sreekanth, A. R.; Mathen, J. S.; Balagopal, L. Acc. Chem. Res. 2003, 36, 899
18. Nair, V.; Dhanya, R.; Rajesh, C.; Bhadbhade, M. M.; Manoj, K. Org. Lett. 2004, 6, 4743
19. Tichenor, M. S.; Kastrinsky, D. B.; Boger, D. L. J. Am. Chem. Soc. 2004, 26, 8396
20. Nair, V.; Dhanya, R.; Rajesh, C.; Devipriya, S. Synlett 2005, 2407
21. Banfield, S. C.; England, D. B.; Kerr, M. A. Org. Lett. 2001, 3, 3325
22. Jackson, S. K.; Banfield, S. C.; Kerr, M. A. Org. Lett. 2005, 7, 1215
23. Quideau, S.; Pouységu, L.; Ozanne, A.; Gagnepain, J. Molecules 2005, 10, 201
24. Jean, A.; Cantat, J.; Bérard, D.; Bouchu, D.; Canesi, S. Org. Lett. 2007, 9, 2553
25. Sabot, C.; Bérard, D.; Canesi, S. Org. Lett. 2008, 10, 4629
26. Giroux, M.-A.; Guérard, K. C.; Beaulieu, M.-A.; Sabot, C.; Canesi, S. Eur. J. Org. Chem. 2009, 3871
27. Wang, L.; Fan, R. Org. Lett. 2012, 13, 3596
28. Trost, B. M. Acc. Chem. Res. 1990, 23, 34
29. Negishi, E.; Copéret, C.; Ma, S.; Liou, S.-Y.; Liu, F. Chem. Rev. 1996, 96, 365
30. Wendt, K. U.; Schulz, G. E.; Corey, E. J.; Liu, D. R. Angew. Chem., Int. Ed. 2000, 39, 2812
31. Diver, S. T.; Giessert, A. J. Chem. Rev. 2004, 104, 1317
32. de Meijere, A.; von Zezschwitz, P.; Bräse, S. Acc. Chem. Res. 2005, 38, 413
33. Yoder, R. A.; Johnston, J. N. Chem. Rev. 2005, 105, 4730
34. Aubert, C.; Fensterbank, L.; Garcia, P.; Malacria, M.; Simonneau, A. Chem. Rev. 2011, 111, 1954
35. Ohno, H. Asian J. Org. Chem. 2013, 2, 18
36. Elassar, A.-Z. A.; El-Khair, A. A. Tetrahedron 2003, 59, 8463
37. Stanovnik, B.; Svete, J. Chem. Rev. 2004, 104, 2433
38. Yang, M.; Tang, J.; Fan, R. Chem. Commun. 2012, 48, 11775
39. Zhang, L.; Li, Z.; Fan, R. Org. Lett. 2012, 14, 6076
40. Zhang, L.; Wang, W.; Fan, R. Org. Lett. 2013, 15, 2018
41. Fujioka, H.; Murai, K.; Kubo, O.; Ohba, Y.; Kita, Y. Org. Lett. 2007, 9, 1687
42. Murai, K.; Nakatani, R.; Kita, Y.; Fujioka, H. Tetrahedron 2008, 64, 11034
43. Murai, K.; Hayashi, S.; Takaichi, N.; Kita, Y.; Fujioka, H. J. Org. Chem. 2009, 74, 1418
44. Bernini, R.; Cacchi, S.; Fabrizi, G.; Filisti, E.; Sferrazza, A. Synlett 2009, 1245
45. Peng, C.; Wang, Y.; Liu, L.; Wang, H.; Zhao, J.; Zhu, Q. Eur. J. Org. Chem. 2010, 818
46. Toh, K. K.; Wang, Y.-F.; Ng, E. P. J.; Chiba, S. J. Am. Chem. Soc. 2011, 133, 13942
47. Toh, K. K.; Sanjaya, S.; Sahnoun, S.; Chong, S. Y.; Chiba, S. Org. Lett. 2012, 14, 2290
48. Xia, X.-F.; Zhang, L.-L.; Song, X.-R.; Liu, X.-Y.; Liang, Y.-M. Org. Lett. 2012, 14, 2480
49. Illuminati, G.; Mandolini, L. Acc. Chem. Res. 1981, 14, 95
50. Evans, P. A.; Holmes, A. B. Tetrahedron 1991, 47, 9131
51. Hoberg, J. O. Tetrahedron 1998, 54, 12631
52. Molander, G. A. Acc. Chem. Res. 1998, 31, 603
53. Yet, L. Chem. Rev. 2000, 100, 2963
54. Galli, C.; Mandolini, L. Eur. J. Org. Chem. 2000, 3117
55. Michaut, A.; Rodriguez, J. Angew. Chem., Int. Ed. 2006, 45, 5740
56. Sharma, A.; Appukkuttan, P.; Eycken, E. V. Chem. Commun. 2012, 48, 1623
57. Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2002, 102, 2523
58. Wirth, T. Hypervalent Iodine Chemistry: Modern Developments in Organic Synthesis Top. Curr. Chem. 2003, 224
59. Ciufolini, M. A.; Braun, N. A.; Canesi, S.; Ousmer, M.; Chang, J.; Chai, D. Synthesis 2007, 3759
60. Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2008, 108, 5299
61. Evans, D. D.; Weale, J.; Weyell, D. J. Aust. J. Chem. 1973, 26, 1333