NHC-catalysed annulation of enals to ene-1,4-diones: Stereoselective synthesis of 1,3-diaryl-4-acyl cyclopentenes

Tetrahedron Letters

Volumn 54, Issue 16, 2013, Pages 2046-2049

  Paul, Rony Rajan ^a   Lakshmi, K C Seetha ^a   Suresh, Eringathodi ^b   Nair, Vijay ^a  

^a REGIONAL RESEARCH LABORATORY CSIR   (India)

^b CSIR CENTRAL SALT AND MARINE CHEMICALS RESEARCH INSTITUTE   (India)

Author keywords

1,3 Diaryl 4 acyl cyclopentenes; Ene 1,4 diones; Homoenolate; N heterocyclic carbene

Indexed keywords

1,3 DIARYL 4 ACYL CYCLOPENTENE; CARBENE; CYCLOPENTENE DERIVATIVE; ENE 1,4 DIONE; HETEROCYCLIC KETONE; N HETEROCYCLIC CARBENE; UNCLASSIFIED DRUG;

ANNULATION REACTION; ARTICLE; STEREOCHEMISTRY; SYNTHESIS;

EID: 84875229364     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2013.01.100     Document Type: Article

References (45)

1. For reviews on NHC chemistry see: V. Nair, S. Bindu, and S. Vellalath Angew. Chem., Int. Ed. 43 2004 5130
2. K. Zeitler Angew. Chem., Int. Ed. 44 2005 7506
3. N. Marion, S. Diez Gonzalez, and S.P. Nolan Angew. Chem., Int. Ed. 46 2007 2988
4. D. Enders, O. Niemeier, and A. Henseler Chem. Rev. 107 2007 5606
5. E.M. Phillips, A. Chan, and K.A. Scheidt Aldrichimica Acta. 42 2009 55
6. J.L. Moore, and T. Rovis B. List, Asymmetric Organocatalysis in Topics in Current Chemistry Vol. 291 2009 Springer Berlin 77
7. P.-C. Chiang, and J.W. Bode N-Heterocyclic Carbenes as Organic Catalysts S. Díez-González, N-Heterocyclic Carbenes: From Laboratory Curiosities to Efficient Synthetic Tools 2010 Royal Society of Chemistry Cambridge 399 RSC Catalysis Series No. 6
8. For reviews on homoenolate chemistry see: V. Nair, S. Vellalath, and B.P. Babu Chem. Soc. Rev. 37 2008 2691
9. V. Nair, R.S. Menon, A.T. Biju, C.R. Sinu, R.R. Paul, A. Jose, and S. Vellalath Chem. Soc. Rev. 40 2011 5336
10. C. Burstein, and F. Glorius Angew. Chem., Int. Ed. 43 2004 6205
11. S.S. Sohn, E.L. Rosen, and J.W. Bode J. Am. Chem. Soc. 126 2004 14370
12. V. Nair, S. Vellalath, M. Poonoth, and E. Suresh J. Am. Chem. Soc. 128 2006 8736
13. V. Nair, R.R. Paul, D.V.M. Padmaja, N. Aiswarya, C.R. Sinu, and A. Jose Tetrahedron 67 2011 9885
14. For related work from other groups: M. Wadamoto, E.M. Phillips, T.E. Reynolds, and K.A. Scheidt J. Am. Chem. Soc. 129 2007 10098
15. P.-C. Chiang, J. Kaeobamrung, and J.W. Bode J. Am. Chem. Soc. 129 2007 3520
16. M. He, and J.W. Bode J. Am. Chem. Soc. 128 2007 418
17. V. Nair, S. Vellalath, M. Poonoth, R. Mohan, and E. Suresh Org. Lett. 8 2006 507
18. V. Nair, S. Vellalath, M. Poonoth, E. Suresh, and S. Viji Synthesis 2007 3195
19. K. Hirano, I. Piel, and F. Glorius Adv. Synth. Catal. 350 2008 984
20. L.-H. Sun, L.-T. Shen, and S. Ye Chem. Commun. 2011 10136
21. A. Chan, and K.A. Scheidt J. Am. Chem. Soc. 130 2008 2741
22. A. Chan, and K.A. Scheidt J. Am. Chem. Soc. 129 2007 5334
23. M. He, and J.W. Bode Org. Lett. 7 2005 3131
24. M. He, and J.W. Bode J. Am. Chem. Soc. 130 2008 418
25. X. Zhao, D.A. DiRocco, and T. Rovis J. Am. Chem. Soc. 133 2011 12466
26. V. Nair, C.R. Sinu, R. Rejithamol, K.C.S. Lakshmi, and E. Suresh Org. Biomol. Chem. 9 2011 5511
27. Y. Jiang, W. Chen, and W. Lu RSC Adv. 2 2012 1540
28. B. Wanner, J. Mahatthananchai, and J.W. Bode Org. Lett. 13 2011 5378
29. V. Nair, B.P. Babu, S. Vellalath, V. Varghese, A.E. Raveendran, and E. Suresh Org. Lett. 11 2009 2507
30. Y. Li, X.-Q. Wang, C. Zheng, and S.-L. You Chem. Commun. 2009 5823
31. V. Nair, S. Vellalath, B.P. Babu, V. Varghese, R.R. Paul, and E. Suresh Org. Biomol. Chem. 8 2010 4861
32. D.T. Cohen, B.C. David, and K.A. Scheidt Angew. Chem., Int. Ed. 50 2011 1678
33. D. Enders, A. Grossmann, H. Huang, and G. Raabe Eur. J. Org. Chem. 2011 4298
34. L. Yang, B. Tan, F. Wang, and G. Zhong J. Org. Chem. 74 2009 1741
35. J. Seayad, P.K. Patra, Y. Zhang, and J.Y. Ying Org. Lett. 10 2008 953
36. V. Nair, C.R. Sinu, B.P. Babu, V. Varghese, A. Jose, and E. Suresh Org. Lett. 11 2009 5570
37. V. Nair, V. Varghese, B.P. Babu, C.R. Sinu, and E. Suresh Org. Biomol. Chem. 8 2010 761
38. V. Nair, B.P. Babu, S. Vellalath, and E. Suresh Chem. Commun. 2008 747
39. V. Nair, R.R. Paul, K.C.S. Lakshmi, R.S. Menon, A. Jose, and C.R. Sinu Tetrahedron Lett. 52 2011 5992
40. For other NHC-catalysed syntheses of pyranones, see: S.J. Ryan, L. Candish, and D.W. Lupton J. Am. Chem. Soc. 126 2004 14370
41. J. Kaeobamrung, M.C. Kozlowski, and J.W. Bode Proc. Natl. Acad. Sci. U.S.A. 107 2010 20661
42. S.D. Sarkar, and A. Studer Angew. Chem., Int. Ed. 49 2010 9266
43. X. Fang, X. Chen, and Y.R. Chi Org. Lett. 13 2011 4080
44. L.R. Domingo, R.J. Zaragozá, and M. Arnó Org. Biomol. Chem. 8 2010 4884
45. P. Verma, P.A. Patni, and R.B. Sunoj J. Org. Chem. 76 2011 5606