Copper-catalyzed tandem alkynylation, propargyl-allenyl isomerization, 6π-electrocyclization of Morita-Baylis-Hillman adducts to naphthalenes

Tetrahedron Letters

Volumn 53, Issue 40, 2012, Pages 5449-5454

  Lim, Jin Woo ^a   Kim, Ko Hoon ^a   Kim, Se Hee ^a   Kim, Jae Nyoung ^a  

^a Chonnam National University   (South Korea)

Author keywords

6 Electrocyclization; Alkynylation; Morita Baylis Hillman adducts; Naphthalenes; Propargyl allenyl isomerization

Indexed keywords

COPPER; NAPHTHALENE;

ALKYNYLATION; ARTICLE; BAYLIS HILLMAN REACTION; CATALYSIS; CYCLIZATION; ISOMERIZATION; SYNTHESIS;

EID: 84865696203     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2012.07.126     Document Type: Article

References (52)

1. For the general reviews on Morita-Baylis-Hillman reaction, see D. Basavaiah, A.J. Rao, and T. Satyanarayana Chem. Rev. 103 2003 811 891
2. D. Basavaiah, B.S. Reddy, and S.S. Badsara Chem. Rev. 110 2010 5447 5674
3. V. Singh, and S. Batra Tetrahedron 64 2008 4511 4574
4. V. Declerck, J. Martinez, and F. Lamaty Chem. Rev. 109 2009 1 48
5. E. Ciganek L.A. Paquette, Organic Reactions Vol. 51 1997 John Wiley & Sons New York 201 350
6. J.N. Kim, and K.Y. Lee Curr. Org. Chem. 6 2002 627 645
7. K.Y. Lee, S. Gowrisankar, and J.N. Kim Bull. Korean Chem. Soc. 26 2005 1481 1490
8. S. Gowrisankar, H.S. Lee, S.H. Kim, K.Y. Lee, and J.N. Kim Tetrahedron 65 2009 8769 8780
9. M. Shi, F.-J. Wang, M.-X. Zhao, and Y. Wei The Chemistry of the Morita-Baylis-Hillman Reaction 2011 RSC Publishing Cambridge, UK
10. For the synthesis of naphthalene derivatives from MBH adducts, see S.H. Kim, S. Lee, H.S. Lee, and J.N. Kim Tetrahedron Lett. 51 2010 6305 6309
11. S.H. Kim, H.S. Lee, K.H. Kim, and J.N. Kim Tetrahedron Lett. 51 2010 4267 4271
12. E.S. Kim, K.H. Kim, S.H. Kim, and J.N. Kim Tetrahedron Lett. 50 2009 5098 5101
13. P.-Y. Chen, H.-M. Chen, L.-Y. Chen, J.-Y. Tzeng, J.-C. Tsai, P.-C. Chi, S.-R. Li, and E.-C. Wang Tetrahedron 63 2007 2824 2828
14. K.Y. Lee, S.C. Kim, and J.N. Kim Tetrahedron Lett. 47 2006 977 980
15. Y.J. Im, K.Y. Lee, T.H. Kim, and J.N. Kim Tetrahedron Lett. 43 2002 4675 4678
16. J.N. Kim, Y.J. Im, J.H. Gong, and K.Y. Lee Tetrahedron Lett. 42 2001 4195 4197
17. S. Gowrisankar, K.Y. Lee, C.G. Lee, and J.N. Kim Tetrahedron Lett. 45 2004 6141 6146
18. For the selected examples on allene-mediated electrocyclization reactions, see J.A. Souto, M. Perez, C.S. Lopez, R. Alvarez, A. Torrado, and A.R. De Lera J. Org. Chem. 75 2010 4453 4462
19. K. Knobloch, and W. Eberbach Eur. J. Org. Chem. 2002 2054 2057
20. F. Wang, X. Tong, J. Cheng, and Z. Zhang Chem. Eur. J. 10 2004 5338 5344
21. S. Tohyama, T. Choshi, K. Matsumoto, A. Yamabuki, K. Ikegata, J. Nobuhiro, and S. Hibino Tetrahedron Lett. 46 2005 5263 5264
22. P. Turnbull, and H.W. Moore J. Org. Chem. 60 1995 3274 3275
23. For the allene-mediated electrocyclization reactions to naphthalene, see H. Zhou, Y. Xing, J. Yao, and Y. Lu J. Org. Chem. 76 2011 4582 4590
24. H. Zhou, Y. Xing, J. Yao, and J. Chen Org. Lett. 12 2010 3674 3677
25. For the similar electrocyclization of aryl enynes, see J. Xu, Y. Wang, and D.J. Burton Org. Lett. 8 2006 2555 2558
26. Y. Wang, and D.J. Burton Org. Lett. 8 2006 5295 5298
27. Y. Wang, and D.J. Burton Tetrahedron Lett. 47 2006 9279 9281
28. Y. Wang, and D.J. Burton J. Fluorine Chem. 128 2007 1052 1057
29. Y. Wang, J. Xu, and D.J. Burton J. Org. Chem. 71 2006 7780 7784
30. For the synthetic applications of propargyl-allenyl isomerizations, see S. Zhu, L. Wu, and X. Huang RSC Adv. 2 2012 132 134
31. J. Cao, and X. Huang Org. Lett. 12 2010 5048 5051
32. X. Huang, S. Zhu, and R. Shen Adv. Synth. Catal. 351 2009 3118 3122
33. R. Shen, L. Chen, and X. Huang Adv. Synth. Catal. 351 2009 2833 2838
34. R. Shen, S. Zhu, and X. Huang J. Org. Chem. 74 2009 4118 4123
35. H. Zhou, D. Zhu, Y. Xie, H. Huang, and K. Wang J. Org. Chem. 75 2010 2706 2709
36. G. Xu, K. Chen, and H. Zhou Tetrahedron Lett. 51 2010 6240 6242
37. For the reaction of Grignard reagents and MBH adducts, see D. Basavaiah, P.K.S. Sarma, and A.K.D. Bhavani J. Chem. Soc., Chem. Commun. 1994 1091 1092
38. Y.S. Song, and K.-J. Lee J. Heterocycl. Chem. 43 2006 1721 1724
39. S. Gowrisankar, K.Y. Lee, S.C. Kim, and J.N. Kim Bull. Korean Chem. Soc. 26 2005 1443 1446
40. Y. Schmidt, and B. Breit Chem. Eur. J. 17 2011 11789 11796
41. For the indium-mediated alkynylation of MBH acetates, see J.S. Yadav, B.V.S. Reddy, N.N. Yadav, A.P. Singh, M. Choudhary, and A.C. Kunar Tetrahedron Lett. 49 2008 6090 6094
42. For the copper-catalyzed coupling of alkynes and allylic or benzylic halides, see L.W. Bieber, and M.F. Da Silva Tetrahedron Lett. 48 2007 7088 7090
43. K.A. Davies, R.C. Abel, and J.E. Wulff J. Org. Chem. 74 2009 3997 4000
44. T. Caruso, and A. Spinella Tetrahedron 59 2003 7787 7790
45. V.V. Grushin, and H. Alper J. Org. Chem. 57 1992 2188 2192
46. For the reaction of MBH adducts and DBU, see Y.J. Im, J.H. Gong, H.J. Kim, and J.N. Kim Bull. Korean Chem. Soc. 22 2001 1053 1055
47. R. Ballini, L. Barboni, G. Bosica, D. Fiorini, E. Mignini, and A. Palmieri Tetrahedron 60 2004 4995 4999
48. For the metal-catalyzed cyclization between aryl moiety and allenyl or acetylenic tether, see X. Zhang, W.T. Teo, and P.W.H. Chan Org. Lett. 11 2009 4990 4993
49. W. Huang, P. Zheng, Z. Zhang, R. Liu, Z. Chen, and X. Zhou J. Org. Chem. 73 2008 6845 6848
50. C. Liu, and R.A. Widenhoefer Org. Lett. 9 2007 1935 1938
51. The stereochemistry of the enyne moiety of compound 7 would be E based on the chemical shift of the vinyl proton (δ = 6.94 ppm) as compared to those of similar compounds, see S.P. Park, S.-H. Ahn, and K.-J. Lee Tetrahedron 66 2010 3490 3498
52. C.R. Reddy, M.D. Reddy, B. Srikanth, and K.R. Prasad Org. Biomol. Chem. 9 2011 6027 6033