Enantioselective organocatalytic conjugate addition of nitroalkanes to electrophilic 2-iminochromenes

ACS Catalysis

Volumn 2, Issue 8, 2012, Pages 1535-1538

  Li, Wenjun ^a   Liu, Hui ^b   Jiang, Xuefeng ^a,b   Wang, Jian ^a  

^a NATIONAL UNIVERSITY OF SINGAPORE   (Singapore)

^b EAST CHINA NORMAL UNIVERSITY   (China)

Author keywords

2 amino 4H chromenes; conjugate addition; nitroalkane; organocatalysis

Indexed keywords

2-AMINO-4H-CHROMENES; CONJUGATE ADDITION; ELECTROPHILES; ENANTIOSELECTIVE; NITROALKANE; NITROALKANES; ORGANOCATALYSIS; ORGANOCATALYTIC;

PARAFFINS; REACTION KINETICS;

ENANTIOSELECTIVITY;

EID: 84864580567     PISSN: 21555435     EISSN: None     Source Type: Journal    
DOI: 10.1021/cs300313j     Document Type: Article

References (35)

1. Harborne, J. B. The Flavanoids-Advances in Research; Chapman & Hall: London, 1988.
2. Parmar, V. S.; Jain, S. C.; Bisht, K. S.; Jain, R.; Taneja, P.; Jha, A.; Tyagi, O. D.; Prasad, A. K.; Wengel, J.; Olsen, C. E.; Boll, P. M. Phytochemistry 1997, 46, 597
3. Bohm, B. A.; Choy, J. B.; Lee, A. Y.-M. Phytochemistry 1989, 28, 501
4. Iacobucci, G. A.; Sweeny, J. G. Tetrahedron 1983, 39, 3005
5. Shen, D.; Shu, M.; Chapman, K. T. Org. Lett. 2000, 2, 2789
6. Anderson, D. R.; Hegde, S.; Reinhard, E.; Gomez, L.; Vernier, W. F.; Lee, L.; Liu, S.; Sambandam, A.; Snider, P. A.; Masih, L. Bioorg. Med. Chem. Lett. 2005, 15, 1587
7. Wang, J. L.; Liu, D.; Zhang, Z.; Shan, S.; Han, X.; Srinvasula, S. M.; Croce, C. M.; Alnemeri, E. S.; Huang, Z. Proc. Natl. Acad. Sci. 2000, 97, 7124
8. Vachal, P.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 10012
9. Okino, T.; Hoashi, Y.; Takemoto, Y. J. Am. Chem. Soc. 2003, 125, 12672
10. Okino, T.; Hoashi, Y.; Furukawa, T.; Xu, Y. T. X. J. Am. Chem. Soc. 2005, 127, 119
11. OReilly, R. A. N. Engl. J. Med. 1976, 295, 354
12. Wingard, L. B.; OReilly, R. A.; Levy, G. Clin. Pharmacol. Ther. 1978, 23, 212
13. Rang, H. P.; Dale, M. M.; Ritter, J. M.; Gardner, P. Pharmacology, 4 th ed.; Churchill Livingston: Philadephia, 2001.
14. Xie, J. W.; Huang, X.; Fan, L. P.; Xu, D. C.; Li, X. S.; Su, H.; Wen, Y. H. Adv. Synth. Catal. 2009, 351, 3077
15. Ramireddy, N.; Abbaraju, S.; Zhao, C. G. Tetrahedron Lett. 2011, 52, 6792
16. Ding, D.; Zhao, C. G. Tetrahedron Lett. 2010, 51, 1322
17. Berkessel, A.; Groger, H. Asymmetric Organocatalysis: From Biomimetic Concepts to Applications in Asymmetric Synthesis; Wiley-VCH: Weinhein, 2005.
18. Dalko, P. I. Enantioselective Organocatalysis: Reactions and Experimental Procedures; Wiley-VCH: Weinhein, 2007.
19. Pinko, P. M. Hydrogen Bonding in Organic Synthesis; Wiley-VCH: Weinhein, 2009.
20. Gao, Y. J.; Ren, Q.; Wu, H.; Li, M. G.; Wang, J. Chem. Commun. 2010, 46, 9232
21. Ren, Q.; Gao, Y. J.; Wang, J. Chem. - Eur. J. 2010, 16, 13594
22. Gao, Y. J.; Ren, Q.; Siau, W.-Y.; Wang, J. Chem. Commun. 2011, 47, 5819
23. Gao, Y. J.; Ren, Q.; Siau, W.-Y.; Wang, J. Org. Biomol. Chem. 2011, 9, 3691
24. Tan, H. R.; Ng, H. F.; Chang, J.; Wang, J. Chem. - Eur. J. 2012, 18, 3865
25. Du, Z.; Siau, W.-Y.; Wang, J. Tetrahedron Lett. 2011, 52, 6137
26. Siau, W.-Y.; Wang, J. Catal. Sci. Technol. 2011, 1, 1298
27. Sigman, M. S.; Jacobsen, E. N. J. Am. Chem. Soc. 1998, 120, 5315
28. Sigman, M. S.; Vachal, P.; Jacobsen, E. Angew. Chem., Int. Ed. 2000, 39, 1279
29. Pihko, P. M Angew. Chem., Int. Ed. 2004, 43, 2062
30. Zuend, S. J.; Matthew, P. C.; Mathieu, P. L.; Jacobsen, E. N. Nature 2009, 461, 968
31. Peschiulli, A.; Procuranti, B.; OConnor, C. J.; Connon, S. J. Nat. Chem. 2010, 2, 380
32. McCooey, S. H.; Connon, S. J. Angew. Chem., Int. Ed. 2005, 44, 6367
33. Vakulya, B.; Varga, S.; Csampai, A.; Soós, T. Org. Lett. 2005, 7, 1967
34. CCDC 871555 (3da) 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.
35. Costa, M.; Areias, F.; Abrunhosa, L.; Venâncio, A.; Proença, F. J. Org. Chem. 2008, 73, 1954