Titanium(IV) chloride-mediated intramolecular ring enlargement of methylenecyclopropanes with propargylic esters: A concise synthesis of bicyclo[4.2.0]oct-5-ene derivatives

Tetrahedron Letters

Volumn 52, Issue 49, 2011, Pages 6541-6544

  Zhang, Zhen ^a   Shi, Min ^a,b  

^a EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

Carbocyclization; Methylenecyclopropanes; Propargylic esters; Ring enlargement; Titanium chloride

Indexed keywords

BICYCLO[4.2.0]OCT 5 ENE DERIVATIVE; CYCLOPROPANE DERIVATIVE; ESTER DERIVATIVE; FUSED ALICYCLIC COMPOUND; METHYLENECYCLOPROPANE DERIVATIVE; TITANIUM TETRACHLORIDE; UNCLASSIFIED DRUG;

ARTICLE; DIASTEREOSELECTIVITY; STEREOCHEMISTRY;

EID: 80555130947     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.09.124     Document Type: Article

References (53)

1. For selected papers on the gold-catalyzed reactions, see: X. Shi, D.J. Gorin, and F.D. Toste J. Am. Chem. Soc. 127 2005 5802 5803
2. L.M. Zhang J. Am. Chem. Soc. 127 2005 16804 16805
3. S.Z. Wang, and L.M. Zhang J. Am. Chem. Soc. 128 2006 8414 8415
4. S.Z. Wang, and L.M. Zhang J. Am. Chem. Soc. 128 2006 14274 14275
5. C.H.M. Amijs, V. López-Carrillo, and A.M. Echavarren Org. Lett. 9 2007 4021 4024
6. E. Jimenez-Nunez, and A.M. Echavarren Chem. Commun. 2007 333 336
7. C.A. Witham, P. Mauleón, N.D. Shapiro, B.D. Sherry, and F.D. Toste J. Am. Chem. Soc. 129 2007 5838 5839
8. M. Yu, G.Z. Zhang, and L.M. Zhang Org. Lett. 9 2007 2147 2150
9. A. Correa, N. Marion, L. Fensterbank, M. Malacria, S.P. Nolan, and L. Cavallo Angew. Chem., Int. Ed. 47 2008 718 721
10. For selected papers on the Pt-catalyzed reactions, see: H.J. Zheng, J.Y. Zheng, B.X. Yu, Q. Chen, X.L. Wang, Y.P. He, Z. Yang, and X.G. She J. Am. Chem. Soc. 132 2010 1788 1789
11. J.K. De Brabander, B. Liu, and M.X. Qian Org. Lett. 10 2008 2533 2536
12. X.Z. Shu, K.G. Ji, S.C. Zhao, Z.J. Zheng, J. Chen, L. Lu, X.Y. Liu, and Y.M. Liang Chem. Eur. J. 14 2008 10556 10559
13. L. Lu, X.Y. Liu, X.Z. Shu, K. Yang, K.G. Ji, and Y.M. Liang J. Org. Chem. 74 2009 474 477
14. V. Rautenstrauch J. Org. Chem. 49 1984 950 952
15. J. Tsuji, and T. Mandai Angew. Chem., Int. Ed. Engl. 34 1995 2589 2612
16. P.H. Dixneuf, T. Guyot, M.D. Ness, and S.M. Roberts Chem. Commun. 1997 2083 2084
17. K. Kato, Y. Yamamoto, and H. Akita Tetrahedron Lett. 43 2002 6587 6590
18. M. Yoshida, M. Fujita, and M. Ihara Org. Lett. 5 2003 3325 3327
19. A. Bartels, R. Mahrwald, and K. Muller Adv. Synth. Catal. 346 2004 483 485
20. M. Yoshida, Y. Morishita, M. Fujita, and M. Ihara Tetrahedron 61 2005 4381 4393
21. R. Riveiros, D. Rodriguez, J.P. Sestelo, and L.A. Sarandeses Org. Lett. 8 2006 1403 1406
22. K. Miki, K. Ohe, and S. Uemura J. Org. Chem. 68 2003 8505 8513
23. K. Miki, K. Ohe, and S. Uemura Tetrahedron Lett. 44 2003 2019 2022
24. A. Tenaglia, and S. Marc J. Org. Chem. 71 2006 3569 3575
25. Y. Shibata, K. Noguchi, and K. Tanaka J. Am. Chem. Soc. 132 2010 7896 7898
26. C. Brancour, T. Fukuyama, Y. Ohta, I. Ryu, A.L. Dhimane, L. Fensterbank, and M. Malacria Chem. Commun. 2010 5470 5472
27. D. Shu, X. Li, M. Zhang, P.J. Robichaux, and W. Tang Angew. Chem., Int. Ed. 50 2011 1346 1349
28. A. Bartels, R. Mahrwald, and S. Quint Tetrahedron Lett. 40 1999 5989 5990
29. R. Mahrwald, and S. Quint Tetrahedron Lett. 42 2001 1655 1656
30. B. Jiang, and Y.G. Si Tetrahedron Lett. 44 2003 6767 6768
31. Z. Zhan, X. Cai, S. Wang, J. Yu, H. Liu, and Y. Cui J. Org. Chem. 72 2007 9838 9841
32. Y. Imada, M. Yuassa, I. Nakamura, and S.I. Murahashi J. Org. Chem. 59 1994 2282 2284
33. For recent reviews, see: J. Marco-Contelles, and E. Soriano Chem. Eur. J. 13 2007 1350 1357
34. N. Marion, and S.P. Nolan Angew. Chem., Int. Ed. 46 2007 2750 2752
35. C. Bruneau Angew. Chem., Int. Ed. 44 2005 2328 2334
36. Z. Zhang, and M. Shi Eur. J. Org. Chem. 2011 2610 2614
37. H. Ohno, T. Mizutani, Y. Kadoh, K. Miyamura, and T. Tanaka Angew. Chem., Int. Ed. 44 2005 5113 5115
38. H. Ohno, T. Mizutani, Y. Kadoh, A. Aso, K. Miyamura, N. Fujii, and T. Tanaka J. Org. Chem. 72 2007 4378 4389
39. O. Kitagawa, T. Suzuki, T. Inoue, and T. Taguchi Tetrahedron Lett. 39 1998 7357 7360
40. O. Kitagawa, T. Suzuki, T. Inoue, Y. Watanabe, and T. Taguchi J. Org. Chem. 63 1998 9470 9475
41. Y. Harrak, A. Simonneau, M. Malacria, V. Gandon, and L. Fensterbank Chem. Commun. 2010 865 867
42. K.G. Ji, X.Z. Shu, S.C. Zhao, H.T. Zhu, Y.N. Niu, X.Y. Liu, and Y.M. Liang Org. Lett. 11 2009 3206 3209
43. K.G. Ji, J. Chen, H.T. Zhu, F. Yang, A. Shaukat, and Y.M. Liang Chem. Eur. J. 17 2011 305 311
44. For slected ring enlargment examples, see: M. Rubin, M. Rubina, and V. Gevorgyan Chem. Rev. 107 2007 3117 3179
45. A. Fürstner, and C. Aïssa J. Am. Chem. Soc. 128 2006 6306 6307
46. M. Shi, L.P. Liu, and J. Tang J. Am. Chem. Soc. 128 2006 7430 7431
47. W. Li, and M. Shi Tetrahedron 63 2007 11016 11020
48. G.Q. Tian, Z.L. Yuan, Z.B. Zhu, and M. Shi Chem. Commun. 2008 2668 2670
49. S.G. Sethofer, S.T. Staben, O.Y. Hung, and F.D. Toste Org. Lett. 10 2008 4315 4318
50. H. Xu, W. Zhang, D. Shu, J.B. Werness, and W. Tang Angew. Chem., Int. Ed. 47 2008 8933 8936
51. S. Ye, and Z.X. Yu Chem. Commun. 2011 794 796
52. L.F. Yao, Y. Wei, and M. Shi J. Org. Chem. 74 2009 9466 9469
53. H.J. Liu, D.Q. Sun, and K.S. Shia Tetrahedron Lett. 37 1996 8073 8076