NHC-catalyzed annulation of enals to 2,4-dien-1-ones: Efficient diastereoselective synthesis of 1,3-diaryl-4-styrenyl cyclopentenes

Synlett

Volumn 24, Issue 13, 2013, Pages 1671-1674

  Sinu, C R ^a   Padmaja, D V M ^a   Jini, P ^a   Lakshmi, K C Seetha ^a   Nair, V ^a  

^a REGIONAL RESEARCH LABORATORY CSIR   (India)

Author keywords

annulation; catalysis; cyclopentene; homoenolate; NHC

Indexed keywords

1,3 DIARYL 4 STYRENYLCYCLOPENTENE DERIVATIVE; 2,4 DIENONE DERIVATIVE; CARBENOID; CHEMICAL COMPOUND; CYCLOPENTENE DERIVATIVE; ENAL DERIVATIVE; HETEROCYCLIC CARBENE DERIVATIVE; NUCLEOPHILE; UNCLASSIFIED DRUG;

ANNULATION REACTION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL ANALYSIS; CHEMICAL INTERACTION; CHEMICAL PHENOMENA; CHEMICAL PROCEDURES; CHEMICAL STRUCTURE; DIASTEREOSELECTIVE SYNTHESIS; SYNTHESIS;

EID: 84880181808     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0033-1339308     Document Type: Article

References (46)

1. Pellissier, H. Tetrahedron 2007, 63, 9267.
2. Mukherjee, S.; Yang, J. W.; Hoffmann, S.; List, B. Chem. Rev. 2007, 107, 5471.
3. MacMillan, D. W. C. Nature (London) 2008, 455, 304.
4. Breslow, R. J. Am. Chem. Soc. 1958, 80, 3719.
5. Stetter, H.; Schreckenberg, M. Angew. Chem., Int. Ed. Engl. 1973, 12, 81.
6. Stetter, H. Angew. Chem., Int. Ed. Engl. 1976, 15, 639.
7. For reviews on NHC-catalyzed reactions, see: Christmann, M. Angew. Chem. Int. Ed. 2005, 44, 2632.
8. Enders, D.; Niemeier, O.; Henseler, A. Chem. Rev. 2007, 107, 5606.
9. Bugaut, X.; Glorius, F. Chem. Soc. Rev. 2012, 41, 3511.
10. Nair, V.; Menon, R. S.; Biju, A. T.; Sinu, C. R.; Paul, R. R.; Jose, A.; Sreekumar, V. Chem. Soc. Rev. 2011, 40, 5336.
11. Moore, J. L.; Rovis, T. Top. Curr. Chem. 2011, 291, 77.
12. Phillips, E. M.; Chan, A.; Scheidt, K. A. Aldrichimica Acta 2009, 42, 55.
13. Chiang, P.-C.; Bode, J. W. In N-Heterocyclic Carbenes: From Laboratory Curiosities to Efficient Synthetic Tools; The Royal Society of Chemistry: Cambridge, 2011, 399.
14. Burstein, C.; Glorius, F. Angew. Chem. Int. Ed. 2004, 43, 6205.
15. Sohn, S. S.; Rosen, E. L.; Bode, J. W. J. Am. Chem. Soc. 2004, 126, 14370.
16. Nair, V.; Vellalath, S.; Poonoth, M.; Mohan, R.; Suresh, E. Org. Lett. 2006, 8, 507.
17. Nair, V.; Vellalath, S.; Poonoth, M.; Suresh, E.; Viji, S. Synthesis 2007, 3195.
18. He, M.; Bode, J. W. Org. Lett. 2005, 7, 3131.
19. Zhang, B.; Feng, P.; Sun, L.-H.; Cui, Y.; Ye, S.; Jiao, N. Chem. Eur. J. 2012, 18, 9198.
20. Nair, V.; Vellalath, S.; Poonoth, M.; Suresh, E. J. Am. Chem. Soc. 2006, 128, 8736.
21. Chiang, P.-C.; Kaeobamrung, J.; Bode, J. W. J. Am. Chem. Soc. 2007, 129, 3520.
22. Wadamoto, M.; Phillips, E. M.; Reynolds, T. E.; Scheidt, K. A. J. Am. Chem. Soc. 2007, 129, 10098.
23. Cardinal-David, B.; Raup, D. E. A.; Scheidt, K. A. J. Am. Chem. Soc. 2010, 132, 5345.
24. Cohen, D. T.; Cardinal- David, B.; Roberts, J. M.; Sarjeant, A. A.; Scheidt, K. A. Org. Lett. 2011, 13, 1068.
25. Nair, V.; Paul, R. R.; Padmaja, D. V. M.; Aiswarya, N.; Sinu, C. R.; Jose, A. Tetrahedron 2011, 67, 9885.
26. Paul, R. R.; Lakshmi, K. C. S.; Suresh, E.; Nair, V. Tetrahedron Lett. 2013, 54, 2046.
27. Chan, A.; Scheidt, K. A. J. Am. Chem. Soc. 2008, 130, 2740.
28. Nair, V.; Babu, B. P.; Vellalath, S.; Varghese, V.; Raveendran, A. E.; Suresh, E. Org. Lett. 2009, 11, 2507.
29. Nair, V.; Sinu, C. R.; Babu, B. P.; Varghese, V.; Jose, A.; Suresh, E. Org. Lett. 2009, 11, 5570.
30. Maji, B.; Ji, L.; Wang, S.; Vedachalam, S.; Ganguly, R.; Liu, X.-W. Angew. Chem. Int. Ed. 2012, 51, 8276.
31. Nair, V.; Varghese, V.; Babu, B. P.; Sinu, C. R.; Suresh, E. Org. Biomol. Chem. 2010, 8, 761.
32. He, M.; Bode, J. W. J. Am. Chem. Soc. 2008, 130, 418.
33. Rommel, M.; Fukuzumi, T.; Bode, J. W. J. Am. Chem. Soc. 2008, 130, 17266.
34. Nair, V.; Poonoth, M.; Vellalath, S.; Suresh, E.; Thirumalai, R. J. Org. Chem. 2006, 71, 8964.
35. Phillips, E.; Reynolds, T.; Scheidt, K. J. Am. Chem. Soc. 2008, 130, 2416.
36. Seayad, J.; Patra, P.; Zhang, Y.; Ying, J. Org. Lett. 2008, 10, 953.
37. Yang, L.; Tan, B.; Wang, F.; Zhong, G. J. Org. Chem. 2009, 74, 1744.
38. Sun, L.-H.; Shen, L.-T.; Ye, S. Chem. Commun. 2011, 47, 10136.
39. Nair, V.; Babu, B. P.; Vellalath, S.; Eringathodi Suresh, E. Chem. Commun. 2008, 747.
40. Nair, V.; Paul, R. R.; Lakshmi, K. C. S.; Menon, R. S.; Jose, A.; Sinu, C. R. Tetrahedron Lett. 2011, 52, 5992.
41. Zhao, X.; DiRocco, D. A.; Rovis, T. J. Am. Chem. Soc. 2011, 133, 12466.
42. Cohen, D. T.; Scheidt, K. A. Chem. Sci. 2012, 3, 53.
43. Struble, J.; Bode, J. W. Tetrahedron 2009, 65, 4957.
44. Sinu, C. R.; Padmaja, D. V. M.; Ranjini, U. P.; Seetha Lakshmi, K. C.; Suresh, E.; Nair, V. Org. Lett. 2013, 15, 68.
45. For theoretical calculations involving DFT studies for the formation of cyclopentenes, see: Domingo, L.; Zaragozá, R.; Arnó, M. Org. Biomol. Chem. 2010, 8, 4884.
46. Verma, P.; Patni, P. A.; Sunoj, R. B. J. Org. Chem. 2011, 76, 5606.