Platinum(IV)-catalyzed regioselective synthesis of highly substituted 4H-cyclopenta[b]furans via cascade heterocyclization of 2-(1-alkynyl)-3-aryl-2- propenals with arylet

Advanced Synthesis and Catalysis

Volumn 355, Issue 2-3, 2013, Pages 365-369

  He, Ting ^a   Gao, Pin ^a   Zhao, Shu Chun ^a   Shi, You Di ^a   Liu, Xue Yuan ^a   Liang, Yong Min ^a  

^a LANZHOU UNIVERSITY   (China)

Author keywords

Cascade reactions; Cyclization; Platinum; Regioselectivity; Transition metal catalysts

Indexed keywords

EID: 84875723838     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201200597     Document Type: Article

References (61)

1. N. Chatani, Directed Metallation, in: Topics in Organometallic Chemistry; Springer, Berlin, 2007
2. Handbook of C-H Transformations, (Ed.: G. Dyker), Wiley-VCH, Weinheim, 2005
3. N. T. Patil, Y. Yamamoto, Chem. Rev. 2008, 108, 3395-3442
4. I. Nakamura, Y. Yamamoto, Chem. Rev. 2004, 104, 2127-2198
5. V. Ritleng, C. Sirlin, M. Pfeffer, Chem. Rev. 2002, 102, 1731-1769
6. M. Rubin, A.W. Sromek, V. Gevorgyan, Synlett 2003, 2265-2291
7. F. Kakiuchi, S. Murai, Acc. Chem. Res. 2002, 35, 826-834.
8. Metal-Catalyzed Cross-Coupling Reactions, (Eds.: F. Diederich, P. J. Stang), Wiley-VCH, New York, 1998
9. nd edn., Vols. 1 and 2 (Eds: A. Meijere, F. Diederich), Wiley-VCH, Chichester, 2004
10. M. Malacria, Chem. Rev. 1996, 96, 289-306
11. M. Victor, H. D. Peter, F. Alosis, Chem. Eur. J. 2004, 10, 4556-4575
12. M. Yoshida, Y. Morishta, M. Fujita, M. Ihara, Tetrahedron 2005, 61, 4381-4393
13. P. A. Inglesby, P. A. Evans, Chem. Soc. Rev. 2010, 39, 2791-2805
14. T. Mark, Y.-H. Du, G. O. Samuel, S. Vishaka, W. Kathryne, T. Lin, S. Michal, L. Pu, J. Am. Chem. Soc. 2011, 133, 11780-11794.
15. R.-L. Yan, H. Yan, C. Ma, Z.-Y. Ren, X.-A. Gao, G.-S. Huang, Y.-M. Liang, J. Org. Chem. 2012, 77, 2024-2028
16. X.-C. Wang, R.-L. Yan, M.-J. Zhong, Y.-M. Liang, J. Org. Chem. 2012, 77, 2064-2068
17. L.-N. Guo, X.-H. Duan, Y.-M. Liang, Acc. Chem. Res. 2011, 44, 111-122
18. X.-F. Xia, X.-Z. Shu, K.-G. Ji, A. Shaukat, X.-Y. Liu, Y.-M. Liang, J. Org. Chem. 2011, 76, 342-345
19. R.-L. Yan, J. Luo, X.-C. Wang, C.-W. Ma, G.-S. Huang, Y.-M. Liang, J. Org. Chem. 2010, 75, 5395-5397
20. X.-F. Xia, X.-Z. Shu, K.-G. Ji, Y.-F. Yang, A. Shaukat, X.-Y. Liu, Y.-M. Liang, J. Org. Chem. 2010, 75, 2893-2902
21. L.-N. Guo, X.-H. Duan, X.-Y. Liu, J. Hu, H.-P. Bi, Y.-M. Liang, Org. Lett. 2007, 9, 5425-5428.
22. B. A. Keay, P. W. Dibble, in: Comprehensive Heterocyclic Chemistry II, Vol. 2, (Eds: A. R. Katritzky, C.W. Rees, E. F. V. Scriven), Pergamon Press, Oxford, 1996, pp 395-436
23. D. M. X. Donnelly, M. J. Meegan, in: Comprehensive Heterocyclic Chemistry, Vol. 4, (Eds.: A. R. Katritzky, C. W. Rees), Pergamon, Oxford, 1984, pp 657-712
24. M. V. Sargent, F. M. Dean, in: Comprehensive Heterocyclic Chemistry, Vol. 4, (Eds: A. R. Katrizky, C. W. Rees), Pergamon Press, New York, 1984, pp 599-656
25. H.-K. Lee, K.-F. Chan, C.-W. Hui, H. K. Yim, X.-W. Wu, H. N. C. Wong, Pure Appl. Chem. 2005, 77, 139-143
26. B. H. Lipshutz, Chem. Rev. 1986, 86, 795-819
27. G. Zeni, R. C. Larock, Chem. Rev. 2004, 104, 2285-2309
28. G. Zeni, R. C. Larock, Chem. Rev. 2007, 107, 303-303.
29. A. F. Pozharskii, A. T. Soldatenkov, A. R. Katritzky, in Heterocycles in Life and Society, Wiley, Chichester, 1997
30. N. Toshiaki, N. Masako, N. Atsushi, J. Am. Chem. Soc. 2003, 125, 7484-7485
31. S. Y. Ian, L.W. Justin, A. K. Michael, Org. Lett. 2005, 7, 953-955
32. S. Y. Ian, A. K. Michael, J. Am. Chem. Soc. 2007, 129, 1465-1469
33. H.-B. Deng, X.-B. Yang, Z.-L. Tong, Z. Li, H.-B. Zhai, Org. Lett. 2008, 10, 1791-1793
34. J. Pavol, M. C. Dane, J. D. Darren, J. Am. Chem. Soc. 2009, 131, 16632-16633
35. I. Fuyuhiko, K. Masahiko, M. Naoki, M. Chisato, Org. Lett. 2010, 12, 1800-1803
36. B. Cheng, F.-F. Wu, X.-B. Yang, Y.-D. Zhou, X.-L. Wan, H.-B. Zhai, Chem. Eur. J. 2011, 17, 12569-12572.
37. W. Skuballa, Angew. Chem. 1981, 93, 1080-1081
38. Angew. Chem. Int. Ed. Engl. 1981, 20, 1046-1048
39. R. C. Nickolson, Tetrahedron Lett. 1983, 24, 47-50.
40. J. Zhang, H. G. Schmalz, Angew. Chem. 2006, 118, 6856-6859
41. Angew. Chem. Int. Ed. 2006, 45, 6704-6707.
42. T.-L. Yao, X.-X. Zhang, R. C. Larock, J. Am. Chem. Soc. 2004, 126, 11164-11165
43. T.-L. Yao, X.-X. Zhang, R. C. Larock, J. Org. Chem. 2005, 70, 7679-7685
44. N. T. Patil, H. Wu, Y. Yamamoto, J. Org. Chem. 2005, 70, 4531-4534
45. N. T. Patil, Y. Yamamoto, ARKIVOC. 2007, 10, 121-141.
46. X. Huang, W.-J. Fu, M.-Z. Miao, Tetrahedron Lett. 2008, 49, 2359-2362.
47. F. E. McDonald, C. C. Schultz, J. Am. Chem. Soc. 1994, 116, 9363-9364.
48. H. D. Scharf, E. Wolters, Chem. Ber. 1978, 111, 639-660.
49. G.-Z. Zhang, X.-G. Huang, G.-T. Li, L.-M. Zhang, J. Am. Chem. Soc. 2008, 130, 1814-1815
50. G.-T. Li, X.-G. Huang, L.-M. Zhang, J. Am. Chem. Soc. 2008, 130, 6944-6945.
51. H.-Y. Gao, J.-L. Zhang, Chem. Eur. J. 2012, 18, 2777-2782
52. L.-F. Wang, R.-H. Fan, Org. Lett. 2012, 14, 3596-3599.
53. A. Fürstner, C. Aissa, J. Am. Chem. Soc. 2006, 128, 6306-6307
54. H.-K. Chang, S. Datta, A. Das, R.-S. Liu, Angew. Chem. 2007, 119, 4828-4831
55. Angew. Chem. Int. Ed. 2007, 46, 4744-4747.
56. CCDC 887445 (3fa) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
57. W. R. Bowman, C. F. Bridge, P. Brookes, M. O. Cloonan, D. C. Leach, J. Chem. Soc. Perkin Trans. 1 2002, 1, 58-68.
58. A. S. K. Hashmi, I. Braun, M. Rudolph, F. Rominger, Organometallics 2012, 31, 644-661.
59. S.-F. Chen, J.-B. Wang, J. Org. Chem. 2007, 72, 4993-4996.
60. M. J. Fuchter, J. N. Levy, Org. Lett. 2008, 10, 4919-4922.
61. J. N. Moorthy, S. Samanta, A. Koner, S. Saha, W. M. Nau, J. Am. Chem. Soc. 2008, 130, 13608-13617.