An efficient synthesis of poly-substituted benzene and tricyclo[3.2.1. 02,7]oct-3-ene derivatives starting from Morita-Baylis-Hillman adducts

Tetrahedron Letters

Volumn 54, Issue 5, 2013, Pages 387-391

  Lim, Cheol Hee ^a   Kim, Sung Hwan ^a   Park, Ka Hyun ^a   Lee, Junseong ^a   Kim, Jae Nyoung ^a  

^a Chonnam National University   (South Korea)

Author keywords

Aerobic oxidation; Diels Alder reaction; Morita Baylis Hillman adducts; Poly substituted benzenes; Tricyclo 3.2.1.02,7 oct 3 enes

Indexed keywords

BROMINE DERIVATIVE; TERPHENYL DERIVATIVE;

AEROBIC METABOLISM; ARTICLE; BAYLIS HILLMAN REACTION; DIELS ALDER REACTION; SUBSTITUTION REACTION; SYNTHESIS; WITTIG REACTION;

ALNUS;

EID: 84871347253     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2012.11.020     Document Type: Article

References (73)

1. For the general review 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 poly-substituted benzenes from MBH adducts, see: P. Xie, Y. Huang, and R. Chen Chem. Eur. J. 18 2012 7362 7366
11. K.N. Clary, M. Parvez, and T.G. Back J. Org. Chem. 75 2010 3751 3760
12. E.S. Kim, K.H. Kim, S.H. Kim, and J.N. Kim Tetrahedron Lett. 50 2009 5098 5101
13. S.C. Kim, K.Y. Lee, H.S. Lee, and J.N. Kim Tetrahedron 64 2008 103 109
14. S.J. Kim, S.H. Kim, K.H. Kim, and J.N. Kim Bull. Korean Chem. Soc. 29 2008 876 878
15. D.Y. Park, K.Y. Lee, S. Gowrisankar, and J.N. Kim Bull. Korean Chem. Soc. 29 2008 701 704
16. D.Y. Park, K.Y. Lee, and J.N. Kim Tetrahedron Lett. 48 2007 1633 1636
17. D.Y. Park, S. Gowrisankar, and J.N. Kim Tetrahedron Lett. 47 2006 6641 6645
18. D.Y. Park, S.J. Kim, T.H. Kim, and J.N. Kim Tetrahedron Lett. 47 2006 6315 6319
19. S.C. Kim, H.S. Lee, Y.J. Lee, and J.N. Kim Tetrahedron Lett. 47 2006 5681 5685
20. M.J. Lee, K.Y. Lee, D.Y. Park, and J.N. Kim Tetrahedron 62 2006 3128 3136
21. M.J. Lee, K.Y. Lee, S. Gowrisankar, and J.N. Kim Tetrahedron Lett. 47 2006 1355 1358
22. J.N. Kim, Y.J. Im, and J.M. Kim Tetrahedron Lett. 43 2002 6597 6600
23. For the synthesis of 1,3-dienes from MBH adducts and their synthetic applications, see: R. Zhou, C. Wang, H. Song, and Z. He Org. Lett. 12 2010 976 979
24. C.G. Lee, K.Y. Lee, S.J. Kim, and J.N. Kim Bull. Korean Chem. Soc. 28 2007 719 720
25. R.M. Crist, P.V. Reddy, and B. Borhan Tetrahedron Lett. 42 2001 619 621
26. C. Muthiah, K.S. Kumar, J.J. Vittal, and K.C.K. Swamy Synlett 2002 1787 1790
27. 2: C, 86.51; H, 5.81. Found: C, 86.29; H, 5.96
28. For the selected Diels-Alder reaction between 1,3-dienes and various dienophiles including DMAD, see: H. Horie, T. Kurahashi, and S. Matsubara Chem. Commun. 48 2012 3866 3868
29. D. Thirion, C. Poriel, J. Rault-Berthelot, F. Barriere, and O. Jeannin Chem. Eur. J. 16 2010 13646 13658
30. M.C. Davis, and T.J. Groshens Synth. Commun. 41 2011 206 218
31. O. Muraoka, G. Tanabe, E. Yamamoto, M. Ono, T. Minematsu, and T. Kimura J. Chem. Soc. Perkin Trans. 1 1997 2879 2890
32. L.F. Fieser, and M.J. Haddadin J. Am. Chem. Soc. 86 1964 2392 2395
33. For the preparation of MBH bromides, see: B. Das, K. Damodar, N. Bhunia, and B. Shashikanth Tetrahedron Lett. 50 2009 2072 2074
34. D. Basavaiah, K.R. Reddy, and N. Kumaragurubaran Nat. Protoc. 2 2007 2665 2676
35. B. Das, J. Banerjee, and N. Ravindranath Tetrahedron 60 2004 8357 8361
36. S. Gowrisankar, S.H. Kim, and J.N. Kim Bull. Korean Chem. Soc. 30 2009 726 728 and further references cited therein
37. 2,7]oct-3-ene skeleton and their synthesis, see: S. Levin, R.R. Nani, and S.E. Reisman J. Am. Chem. Soc. 133 2011 774 776
38. C.-C. Tseng, H. Ding, A. Li, Y. Guan, and D.Y.-K. Chen Org. Lett. 13 2011 4410 4413
39. S.W. Pelletier, N.V. Mody, Z. Djarmati, and S.D. Lajsic J. Org. Chem. 41 1976 3042 3044
40. S.M. Ng, C.M. Beaudry, and D. Trauner Org. Lett. 5 2003 1701 1704
41. A. Leverrier, M.-T. Martin, C. Servy, J. Ouazzani, P. Retailleau, K. Awang, M.R. Mukhtar, F. Gueritte, and M. Litaudon J. Nat. Prod. 73 2010 1121 1125
42. Y.J. Hong, and D.J. Tantillo J. Am. Chem. Soc. 132 2010 5375 5386
43. E.J. Corey, G. Wess, Y.B. Xiang, and A.K. Singh J. Am. Chem. Soc. 109 1987 4717 4718
44. S. Zhu, L. Wu, and X. Huang RSC Adv. 2 2012 132 134
45. J. Barluenga, E. Tudela, R. Vicente, A. Ballesterous, and M. Tomas Angew. Chem., Int. Ed. 50 2011 2107 2110
46. T.-C. Wu, J.-J. Chen, and Y.-T. Wu Org. Lett. 13 2011 4794 4797
47. K. Yamaguchi, M. Eto, Y. Yoshitake, and K. Harano Chem. Pharm. Bull. 57 2009 749 751
48. D. Skropeta, and R.W. Rickards Tetrahedron Lett. 48 2007 3281 3284
49. G. Mehta, and C. Ravikrishna Tetrahedron Lett. 37 1996 2655 2658
50. R.A. Brand, and J.E. Mulvaney J. Org. Chem. 45 1980 633 636
51. 2f,4a For some additional references on the base-mediated aerobic oxidations, see: S.-i. Ikeda, N. Mori, and Y. Sato J. Am. Chem. Soc. 119 1997 4779 4780
52. M.V. Gil, E. Roman, and J.A. Serrano Tetrahedron Lett. 42 2001 4625 4628
53. S.H. Kim, H.S. Lee, B.R. Park, and J.N. Kim Bull. Korean Chem. Soc. 32 2011 1725 1728
54. For the similar successive conjugate addition reaction, see: B. Hu, L.-G. Meng, Y.-L. Liu, M. Liang, and S. Xue Synthesis 2009 4137 4142
55. K. Takasu, S. Mizutani, M. Noguchi, K. Makita, and M. Ihara J. Org. Chem. 65 2000 4112 4119
56. H. Hagiwara, Y. Yamada, H. Sakai, T. Suzuki, and M. Ando Tetrahedron 54 1998 10999 11010
57. M. Ihara, and K. Fukumoto Angew. Chem., Int. Ed. 32 1993 1010 1022
58. J.A. MacKay, Z.C. Landis, S.E. Motika, and M.H. Kench J. Org. Chem. 77 2012 7768 7774
59. T. Hata, H. Imade, and H. Urabe Org. Lett. 14 2012 2450 2453
60. For the synthesis and applications of oligoarenes including quaterphenyls and quinquephenyls, see: Z. Dong, X. Liu, G.P.A. Yap, and J.M. Fox J. Org. Chem. 72 2007 617 625
61. S. Ishikawa, and K. Manabe Chem. Commun. 2006 2589 2591
62. M.W. Read, J.O. Escobedo, D.M. Willis, P.A. Beck, and R.M. Strongin Org. Lett. 2 2000 3201 3204
63. M. Wang, F. Han, H. Yuan, and Q. Liu Chem. Commun. 46 2010 2247 2249
64. B.R. Hsieh, W.C. Wan, Y. Yu, Y. Gao, T.E. Goodwin, S.A. Gonzalez, and W.A. Feld Macromolecules 31 1998 631 636
65. For some selected examples of Diels-Alder reaction with N-substituted maleimides, see: X.-F. Xiong, Q. Zhou, J. Gu, L. Dong, T.-Y. Liu, and Y.-C. Chen Angew. Chem., Int. Ed. 51 2012 4401 4404
66. F. Tripoteau, T. Verdelet, A. Hercouet, F. Carreaux, and B. Carboni Chem. Eur. J. 17 2011 13670 13675
67. M.J. Jacobsen, E.D. Funder, J.R. Cramer, and K.V. Gothelf Org. Lett. 13 2011 3418 3421
68. A. Aljarilla, M.C. Murcia, A.G. Csaky, and J. Plumet Eur. J. Org. Chem. 2009 822 832
69. H. Urabe, K. Kusaka, D. Suzuki, and F. Sato Tetrahedron Lett. 43 2002 285 289
70. For the synthesis of polyarylphthalimides, see: R. Vanel, F. Berthiol, B. Bessieres, C. Einhorn, and J. Einhorn Synlett 2011 1293 1295
71. L.X. Alvarez, B. Bessieres, and J. Einhorn Synlett 2008 1376 1380
72. L. Ding, H.-Z. Ying, Y. Zhou, T. Lei, and J. Pei Org. Lett. 12 2010 5522 5525
73. Y. Nishina, T. Kida, and T. Ureshino Org. Lett. 13 2011 3960 3963