Enantioselective organocatalytic Biginelli reaction: Dependence of the catalyst on sterics, hydrogen bonding, and reinforced chirality

Journal of Organic Chemistry

Volumn 76, Issue 2, 2011, Pages 396-402

  Saha, Satyajit ^a   Moorthy, Jarugu Narasimha ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY KANPUR   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ALIPHATIC ALDEHYDES; BIGINELLI REACTION; CYCLOCONDENSATION; ENANTIOSELECTIVE; ETHYLACETOACETATE; HIGH ENANTIOSELECTIVITY; HYDROGEN BONDINGS; ORGANOCATALYSTS; ORGANOCATALYTIC; STERICS; SYSTEMATIC INVESTIGATIONS;

ALDEHYDES; CATALYSTS; CHIRALITY; ENANTIOMERS; ENANTIOSELECTIVITY; HYDROGEN; HYDROGEN BONDS; SYNTHESIS (CHEMICAL); UREA;

STEREOCHEMISTRY;

4 TOSYLAMIDO N (2,4,6 TRIETHYLPHENYL)PYRROLIDINE 2 CARBOXAMIDE; ALDEHYDE; AMIDE; UNCLASSIFIED DRUG;

ARTICLE; BIGINELLI REACTION; CATALYSIS; CATALYST; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOSELECTIVITY; HYDROGEN BOND; SYNTHESIS;

EID: 78651512142     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo101717m     Document Type: Article

References (36)

1. Enders, D.; Grondal, C.; Huttl, M. R. M. Angew. Chem., Int. Ed. 2007, 46, 1570
2. Tietze, L. F.; Beifuss, U. Angew. Chem., Int. Ed. Engl. 1993, 32, 131
3. Tietze, L. F. Chem. Rev. 1996, 96, 115
4. Tietze, L. F.; Haunert, F. In Stimulating Concepts in Chemistry; Vogtle, F.; Stoddart, J. F.; Shibasaki, M., Eds.; Wiley-VCH: Weinheim, Germany, 2000; p 39.
5. Nicolaou, K. C.; Montagnon, T.; Snyder, S. A. Chem. Commun. 2003, 551
6. Wasilke, J.-C.; Obrey, S. J.; Baker, R. T.; Bazan, G. C. Chem. Rev. 2005, 105, 1001
7. Ramkn, D. J.; Yus, M. Angew. Chem., Int. Ed. 2005, 44, 1602
8. Guo, H.-C.; Ma, J.-A. Angew. Chem., Int. Ed. 2006, 45, 354
9. Pellissier, H. Tetrahedron 2006, 62, 1619
10. Pellisier, H. Tetrahedron 2006, 62, 2143
11. Tietze, L. F.; Brasche, G.; Gerike, K. Domino Reactions in Organic Chemistry; Wiley-VCH: Weinheim, Germany, 2006.
12. Biginelli, P. Gazz. Chim. Ital. 1893, 23, 360
13. Dondoni, D.; Massi, A. Acc. Chem. Res. 2006, 39, 451
14. Kappe, C. O. In Multicomponent Reactions; Zhu, J.; Bienaymq, H., Eds.; Wiley-VCH: Weinheim, Germany, 2005; p 95.
15. Kappe, C. O. Acc. Chem. Res. 2000, 33, 879
16. Simon, C.; Constantieux, T.; Rodriguez, J. Eur. J. Org. Chem. 2004, 4957
17. Taylor, M. S.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2006, 45, 1520
18. Connon, S. J. Angew. Chem., Int. Ed. 2006, 45, 3909
19. Hurst, E. W. Ann. N. Y. Acad. Sci. 1962, 98, 275
20. Kappe, C. O. Eur. J. Med. Chem. 2000, 35, 1043
21. Atwal, K. S.; Rovnyak, G. C.; Kimball, S. D.; Floyd, D. M.; Moreland, S.; Swanson, B. N.; Gougoutas, J. Z.; Schwartz, J.; Smillie, K. M.; Malley, M. F. J. Med. Chem. 1990, 33, 2629
22. Atwal, K. S.; Swanson, B. N.; Unger, S. E.; Floyd, D. M.; Moreland, S.; Hedberg, A.; Orreilly, B. C. J. Med. Chem. 1991, 34, 806
23. Dondoni, A.; Massi, A.; Sabbatini, S. Tetrahedron Lett. 2002, 43, 5913
24. Kappe, C. O.; Uray, G.; Roschger, P.; Lindner, W.; Kratky, C.; Keller, W. Tetrahedron 1992, 48, 5473
25. Sidler, D. R.; Barta, N.; Li, W.; Hu, E.; Matty, L.; Ikemoto, N.; Campbell, J. S.; Chartrain, M.; Gbewonyo, K.; Boyd, R.; Corley, E. G.; Ball, R. G.; Larsen, R. D.; Reider, P. J. Can. J. Chem. 2002, 80, 646
26. Kappe, C. O.; Uray, G.; Roschger, P.; Lindner, W.; Kratky, C.; Keller, W. Tetrahedron 1992, 48, 5473
27. Xin, J. G.; Chang, L.; Hou, Z. R.; Shang, D. J.; Liu, X. H.; Feng, X. M. Chem.-Eur. J. 2008, 14, 3177
28. Wu, Y.-Y.; Chai, Z.; Liu, X.-Y.; Zhao, G.; Wang, S.-W. Eur. J. Org. Chem. 2009, 904
29. Wang, Y.; Yang, H.; Yu, J.; Miao, Z.; Chen, R. Adv. Synth. Catal. 2009, 351, 3057
30. Olvera, R. D.; Demare, P.; Regla, I.; Juaristi, E. ARKIVOC 2008, 61
31. Moorthy, J. N.; Saha, S. Eur. J. Org. Chem. 2009, 739
32. Saha, S.; Moorthy, J. N. Tetrahedron Lett. 2010, 51, 912
33. Saha, S.; Seth, S.; Moorthy, J. N. Tetrahedron Lett. 2010, 51, 5281
34. Moorthy, J. N.; Saha, S. Eur. J. Org. Chem. 2010, 6359
35. Dahlin, N.; Bogevig, A.; Adolfsson, H. Adv. Synth. Catal. 2004, 346, 1101
36. Chen, X.-H.; Xu, X.-Y.; Liu, H.; Cun, L.-F.; Gong, L.-Z. J. Am. Chem. Soc. 2006, 128, 14802