Controlled synthesis of 1-vinylnaphthalenes versus (E)-α-(1,3-enyn-4- yl)-α,β-unsaturated esters from Morita-Baylis-Hillman bromides: A sequential alkynylation and competitive 6π-electrocyclization versus conjugative transposition of a triple bond

Tetrahedron Letters

Volumn 54, Issue 21, 2013, Pages 2595-2599

  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; Dienynes; Morita Baylis Hillman bromides; Vinylnaphthalenes

Indexed keywords

1 METHYLNAPHTHALENE; 1 VINYLNAPHTHALENE; 4 NITROPHENYL PROPARGYL ETHER; ACETIC ACID; ALPHA(1,3 ENYN 4 YL) ALPHA,BETA UNSATURATED ESTER; BROMINE DERIVATIVE; DIENYNE; PROPARGYL ACETATE; UNCLASSIFIED DRUG;

ALKYNYLATION; ARTICLE; BAYLIS HILLMAN REACTION; CHEMICAL BOND; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; CONJUGATIVE TRANSPOSITION; CONTROLLED STUDY; CYCLIZATION; ELECTROCYCLIZATION; SYNTHESIS; TEMPERATURE; TRIPLE BOND;

EID: 84876417928     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2013.03.007     Document Type: Article

References (59)

1. For the synthesis and synthetic applications of α-ethynyl-α, β-unsaturated esters, see: A.B. Lemay, K.S. Vulic, and W.W. Ogilvie J. Org. Chem. 71 2006 3615 3618
2. R. Rossi, F. Bellina, C. Bechini, L. Mannina, and P. Vergamini Tetrahedron 54 1998 135 156
3. W.-M. Dai, Jinlong Wu, K.C. Fong, M.Y.H. Lee, and C.W. Lau J. Org. Chem. 64 1999 5062 5082
4. W.-M. Dai, A. Wu, and W. Hamaguchi Tetrahedron Lett. 42 2001 4211 4214
5. T. Hirabayashi, S. Sakaguchi, and Y. Ishii Adv. Synth. Catal. 347 2005 872 876
6. M. Cai, X. Fang, R. Dai, and L. Zha Appl. Organomet. Chem. 23 2009 229 234
7. Y. Choe, and P.H. Lee Org. Lett. 11 2009 1445 1448
8. H. Kim, D. Shin, K. Lee, S. Lee, S. Kim, and P.H. Lee Bull. Korean Chem. Soc. 31 2010 742 745
9. B.M. Trost, J.L. Gunzner, and T. Yasukata Tetrahedron Lett. 42 2001 3775 3778
10. X. Yu, H. Ren, Y. Xiao, and J. Zhang Chem. Eur. J. 14 2008 8481 8485
11. X. Yu, G. Zhou, and J. Zhang Chem. Commun. 48 2012 4002 4004
12. Y. Deng, X. Jin, C. Fu, and S. Ma Org. Lett. 11 2009 2169 2172
13. B. Alcaide, P. Almendros, and T. Martinez del Campo Org. Biomol. Chem. 10 2012 7603 7609
14. X. Yu, and J. Zhang Adv. Synth. Catal. 353 2011 1265 1268
15. G. Zhou, F. Liu, and J. Zhang Chem. Eur. J. 17 2011 3101 3104
16. H. Gao, X. Wu, and J. Zhang Chem. Eur. J. 17 2011 2838 2841
17. T. Wang, and J. Zhang Chem. Eur. J. 17 2011 86 90
18. X. Yu, B. Du, K. Wang, and J. Zhang Org. Lett. 12 2010 1876 1879
19. F. Liu, D. Qian, L. Li, X. Zhao, and J. Zhang Angew. Chem., Int. Ed. 49 2010 6669 6672 and further references cited therein
20. A. Tikad, A. Hamze, O. Provot, J.-D. Brion, and M. Alami Eur. J. Org. Chem. 2010 725 731
21. N. Tsukada, S. Ninomiya, Y. Aoyama, and Y. Inoue Org. Lett. 9 2007 2919 2921
22. Y. Wang, and D.J. Burton Org. Lett. 8 2006 5295 5298
23. S. Tsuboi, H. Kuroda, S. Takatsuka, T. Fukawa, T. Sakai, and M. Utaka J. Org. Chem. 58 1993 5952 5957
24. X. Yu, and J. Zhang Chem. Eur. J. 18 2012 12945 12949
25. W. Li, Y. Li, G. Zhou, X. Wu, and J. Zhang Chem. Eur. J. 18 2012 15113 15121
26. Y. Zou, and J.G. Millar Tetrahedron Lett. 51 2010 1336 1337
27. J.G. Millar, M. Hoddle, J.S. McElfresh, Y. Zou, and C. Hoddle Tetrahedron Lett. 49 2008 4820 4823
28. S. Pantke-Bocker, G. Pohnert, I. Fischer-Lui, and W. Boland Tetrahedron 51 1995 7927 7936
29. F. Tellier, C. Descoins, and R. Sauvetre Tetrahedron 47 1991 7767 7774
30. B.P. Andreini, and M. Benetti Tetrahedron 43 1987 4591 4600
31. F.M. Istrate, and F. Gagosz Org. Lett. 9 2007 3181 3184
32. D. Liotta, D. Brown, W. Hoekstra, and R. Monahan III Tetrahedron Lett. 28 1987 1069 1072
33. D. Basavaiah, A.J. Rao, and T. Satyanarayana Chem. Rev. 103 2003 811 891
34. D. Basavaiah, B.S. Reddy, and S.S. Badsara Chem. Rev. 110 2010 5447 5674
35. V. Singh, and S. Batra Tetrahedron 64 2008 4511 4574
36. V. Declerck, J. Martinez, and F. Lamaty Chem. Rev. 109 2009 1 48
37. J.N. Kim, and K.Y. Lee Curr. Org. Chem. 6 2002 627 645
38. K.Y. Lee, S. Gowrisankar, and J.N. Kim Bull. Korean Chem. Soc. 26 2005 1481 1490
39. S. Gowrisankar, H.S. Lee, S.H. Kim, K.Y. Lee, and J.N. Kim Tetrahedron 65 2009 8769 8780
40. M. Shi, F.-J. Wang, M.-X. Zhao, and Y. Wei The Chemistry of the Morita-Baylis-Hillman Reaction 2011 RSC Publishing Cambridge, UK
41. J.W. Lim, K.H. Kim, S.H. Kim, and J.N. Kim Tetrahedron Lett. 53 2012 5449 5454
42. For the synthesis and synthetic applications of vinylnaphthalenes, see: N. Iwasawa, M. Otsuka, S. Yamashita, M. Aoki, and J. Takaya J. Am. Chem. Soc. 130 2008 6328 6329
43. Y. Hayashida, Y. Nakamura, Y. Chida, and J. Nishimura Tetrahedron Lett. 40 1999 6435 6438
44. Y. Nakamura, M. Matsumoto, Y. Hayashida, and J. Nishimura Tetrahedron Lett. 38 1997 1983 1986
45. K.L. Reddy, K.R. Dress, and K.B. Sharpless Tetrahedron Lett. 39 1998 3667 3670
46. F.-C. Huang, W.-K. Chan, J.D. Warus, M.M. Morrissette, K.J. Moriarty, M.N. Chang, J.J. Travis, L.S. Mitchell, G.W. Nuss, and C.A. Sutherland J. Med. Chem. 35 1992 4253 4255
47. S.R. Kasibhatla, B.C. Bookser, W. Xiao, and M.D. Erion J. Med. Chem. 44 2001 613 618
48. For the elimination of p-nitrophenol to form an alkene, see: B.H. Lipshutz, S. Ghorai, and Z.V. Boskovic Tetrahedron 64 2008 6949 6954
49. For the examples on 6π-electrocyclization at room temperature, see: H. Zhou, Y. Xing, J. Yao, and J. Chen Org. Lett. 12 2010 3674 3677
50. H. Zhou, Y. Xing, J. Yao, and Y. Lu J. Org. Chem. 76 2011 4582 4590
51. For the selected examples on propargyl-allenyl isomerization, see: Y. Xing, Y. Wei, and H. Zhou Curr. Org. Chem. 16 2012 1594 1608 and further references cited therein
52. J. Xu, Y. Wang, and D. Burton J. Org. Lett. 8 2006 2555 2558
53. R. Shen, S. Zhu, and X. Huang J. Org. Chem. 74 2009 4118 4123
54. X. Huang, S. Zhu, and R. Shen Adv. Synth. Catal. 351 2009 3118 3122
55. For the 1,4-elimination of acetic acid from allenylmethyl acetate (or tosylate), see: B.M. Trost, and J.M. Tour J. Org. Chem. 54 1989 484 486
56. A.J. Bridges, and J.W. Fischer J. Chem. Soc., Chem. Commun. 1982 665 666
57. T.G. Back, E.K.Y. Lai, and K.R. Muralidharan J. Org. Chem. 55 1990 4595 4602
58. S. Kitagaki, S. Teramoto, and C. Mukai Org. Lett. 9 2007 2549 2552
59. For the isomerization of propargyl amides to ynamides via the corresponding allenyl amides, see: J. Huang, H. Xiong, R.P. Hsung, C. Rameshkumar, J.A. Mulder, and T.P. Grebe Org. Lett. 4 2002 2417 2420