Asymmetric formation of bridged benzoxazocines through an organocatalytic multicomponent dienamine-mediated one-pot cascade

Organic Letters

Volumn 16, Issue 16, 2014, Pages 4182-4185

  Ransborg, Lars Krogager ^a   Overgaard, Mette ^a   Hejmanowska, Joanna ^b   Barfüsser, Sebastian ^a   Jørgensen, Karl Anker ^a   Albrecht, Łukasz ^b  

^a AARHUS UNIVERSITY   (Denmark)

^b LODZ UNIVERSITY OF TECHNOLOGY   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84906270562     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol501882x     Document Type: Article

References (31)

1. Schreiber, S. L. Science 2000, 287, 1964
2. Enders, D.; Grondal, C.; Hüttl, M. R. M. Angew. Chem., Int. Ed. 2007, 46, 1570
3. Albrecht, L.; Jiang, H.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2011, 50, 8492
4. Ramachary, D. B.; Jain, S. Org. Biomol. Chem. 2011, 9, 1277
5. Patil, N. T.; Shinde, V. S.; Gajula, B. Org. Biomol. Chem. 2012, 10, 211
6. Wende, R. C.; Schreiner, P. R. Green Chem. 2012, 14, 1821
7. Melchiorre, P.; Marigo, M.; Carlone, A.; Bartoli, G. Angew. Chem., Int. Ed. 2008, 47, 6138
8. Melchiorre, P. Angew. Chem., Int. Ed. 2012, 51, 9748
9. Jensen, K. L.; Dickmeiss, G.; Jiang, H.; Albrecht, Å.; Jørgensen, K. A. Acc. Chem. Res. 2012, 45, 248
10. Li, J.-L.; Liu, T.-Y.; Chen, Y.-C. Acc. Chem. Res. 2012, 45, 1491
11. Ramachary, D. B.; Reddy, Y. V. Eur. J. Org. Chem. 2012, 865
12. Jiang, H.; Albrecht, Å.; Jørgensen, K. A. Chem. Sci. 2013, 4, 2287
13. Jurberg, I. D.; Chatterjee, I.; Tannert, R.; Melchiorre, P. Chem. Commun. 2013, 49, 4869
14. For a seminal report, see: Bertelsen, S.; Marigo, M.; Brandes, S.; Dinér, P.; Jørgensen, K. A. J. Am. Chem. Soc. 2006, 128, 12973
15. Hong, B.-C.; Wu, M.-F.; Tseng, H.-C.; Huang, G.-F.; Su, C.-F.; Liao, J.-H. J. Org. Chem. 2007, 72, 8459
16. Hong, B.-C.; Tseng, H.-C.; Chen, S.-H. Tetrahedron 2007, 63, 2840
17. deFigueiredo, R. M.; Fröhlich, R.; Christmann, M. Angew. Chem., Int. Ed. 2008, 47, 1450
18. Han, B.; He, Z.-Q.; Li, J.-L.; Li, R.; Jiang, K.; Liu, T.-Y.; Chen, Y.-C. Angew. Chem., Int. Ed. 2009, 48, 5474
19. Li, J.-L.; Kang, T.-R.; Zhou, S.-L.; Li, R.; Wu, L.; Chen, Y.-C. Angew. Chem., Int. Ed. 2010, 49, 6418
20. Li, J.-L.; Zhou, S.-L.; Chen, P.-X.; Dong, L.; Liu, T.-Y.; Chen, Y.-C. Chem. Sci. 2012, 3, 1879
21. Talavera, G.; Reyes, E.; Vicario, J. L.; Carrillo, L. Angew. Chem., Int. Ed. 2012, 51, 4104
22. Albrecht, Å.; Dickmeiss, G.; Cruz Acosta, F.; Rodríguez- Escrich, C.; Davis, R. L.; Jørgensen, K. A. J. Am. Chem. Soc. 2012, 134, 2543
23. Albrecht, Å.; Dickmeiss, G.; Weise, C. F.; Rodríguez- Escrich, C.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2012, 51, 13109
24. Liu, K.; Chougnet, A.; Woggon, W.-D. Angew. Chem., Int. Ed. 2008, 47, 5827
25. Orue, A.; Reyes, E.; Vicario, J. L.; Carrillo, L.; Uria, U. Org. Lett. 2012, 14, 3740
26. Narjes, F.; Crescenzi, B.; Ferrara, M.; Habermann, J.; Colarusso, S.; Ferreira, M.; Stansfield, I.; Mackay, A.; Conte, I.; Ercolani, C.; Zaramella, S.; Palumbi, M.; Meuleman, P.; Leroux-Roels, G.; Giuliano, C.; Fiore, F.; Di Marco, S.; Baiocco, P.; Koch, U.; Migliaccio, G.; Altamura, S.; Laufer, R.; DeFrancesco, R.; Rowley, M. J. Med. Chem. 2011, 54, 289
27. Raj, K. R.; Harry, G. P. Beecham Group LTD, DE1908324-(A1), 19690911.
28. Razdan, R. K.; Pars, H. G.; Zitko, B. A.; Kane, V. V.; Thompson, W. R. Tetrahedron Lett. 1973, 14, 1623
29. Sahn, J. J.; Su, J. Y.; Martin, S. F. Org. Lett. 2011, 13, 2590
30. Sahn, J. J.; Martin, S. F. Tetrahedron Lett. 2011, 52, 6855
31. See Supporting Information for details. CCDC 1009470 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.