Facile synthesis of tetrahydro-1 H-isoindolones via a sequential three-component copper-catalyzed coupling/propargyl-allenyl isomerization/[4 + 2] cyclization reaction

Organic Letters

Volumn 12, Issue 21, 2010, Pages 5048-5051

  Cao, Jian ^a   Huang, Xian ^a,b  

^a ZHEJIANG UNIVERSITY   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 78049511627     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol102235t     Document Type: Article

References (54)

1. Wasilke, J.-C.; Obrey, S. J.; Baker, R. T.; Bazan, G. C. Chem. Rev. 2005, 105, 1001
2. Lee, J. M.; Na, Y.; Han, H.; Chang, S. Chem. Soc. Rev. 2004, 33, 302
3. Montgomery, J. Acc. Chem. Res. 2000, 33, 467
4. Ikeda, S. I. Acc. Chem. Res. 2000, 33, 511
5. Tietze, L. F. Chem. Rev. 1996, 96, 115
6. Bunce, R. A. Tetrahedron 1995, 51, 13103
7. Patai, S. The Chemistry of Ketenes, Allenes, and Related Compounds; John Wiley & Sons: New York, 1980.
8. Schuster, H. F.; Coppola, G. M. Allenes in Organic Synthesis; John Wiley & Sons: New York, 1984.
9. Landor, S. R. The Chemistry of Allenes; Academic Press: New York, 1982; Vols. 1-3.
10. Krause, N.; Hashmi, A. S. K. Modern Allene Chemistry; Wiley-VCH: Weinheim, Germany, 2004; Vols. 1-2.
11. Ma, S. Chem. Rev. 2005, 105, 2829
12. Ma, S. Acc. Chem. Res. 2003, 36, 701
13. Ma, S. Acc. Chem. Res. 2009, 42, 1679
14. Ma, S. Eur. J. Org. Chem. 2004, 1175
15. Ma, S. Aldrichimica Acta 2007, 40, 91
16. Marshall, J. A. Chem. Rev. 1996, 96, 31
17. Yamamoto, Y.; Radhakrishnan, U. Chem. Soc. Rev. 1999, 28, 199
18. Zimmer, R.; Dinesh, C. U.; Nandanan, E.; Khan, F. A. Chem. Rev. 2000, 100, 3067
19. Marshall, J. Chem. Rev. 2000, 100, 3163
20. Ma, S.; Lu, P.; Lu, L.; Hou, H.; Wei, J.; He, Q.; Gu, Z.; Jiang, X.; Jin, X. Angew. Chem., Int. Ed. 2005, 44, 5275
21. Jiang, X.; Kong, W.; Chen, J.; Ma, S. Org. Biomol. Chem. 2008, 6, 3606
22. Padwa, A.; Meske, M.; Murphree, S. S.; Watterson, S. H.; Ni, Z. J. Am. Chem. Soc. 1995, 117, 7071
23. Wender, P. A.; Jenkins, T. E.; Suzuki, S. J. Am. Chem. Soc. 1995, 117, 1843
24. Padwa, A.; Filipkowski, M. A.; Meske, M.; Watterson, S. H.; Ni, Z. J. Am. Chem. Soc. 1993, 115, 3776
25. Kanematsu, K.; Sugimoto, N.; Kawaoka, M.; Yeo, S.; Shiro, M. Tetrahedron Lett. 1991, 32, 1351
26. Braun, R. U.; Ansorge, M.; Müller, T. J. J. Chem.-Eur. J. 2006, 12, 9081
27. Braun, R. U.; Zeitler, K.; Müller, T. J. J. Org. Lett. 2001, 3, 3297
28. D'Souza, D. M.; Kiel, A.; Herten, D. P.; Müller, T. J. J. Chem.-Eur. J. 2008, 14, 529
29. Braun, R. U.; Zeitler, K.; Müller, T. J. J. Org. Lett. 2000, 2, 4181
30. D'Souza, D. M.; Rominger, F.; Müller, T. J. J. Angew. Chem., Int. Ed. 2005, 44, 153
31. D'Souza, D. M.; Rominger, F.; Müller, T. J. J. Chem. Commun. 2006, 4096
32. Shen, R.; Huang, X. Org. Lett. 2008, 10, 3283
33. Shen, R.; Huang, X.; Chen, L. Adv. Synth. Catal. 2008, 350, 2865
34. Sha, F.; Huang, X. Angew. Chem., Int. Ed. 2009, 48, 3458
35. Jiang, J.; Devita, R. J.; Kumar, S.; Mills, S. G.; Tschirret-Guth, R. A. Int. Patent WO 2007002457, 2007.
36. Kuethe, J. T.; Yin, J.; Huffman, M. A.; Journet, M. Int. Patent WO 2007008564, 2007.
37. Rudd, J. A.; Ngan, M. P.; Wai, M. K. Eur. J. Pharmacol. 1999, 366, 243
38. Walling, E. A.; Drafft, G. A.; Ware, B. R. Arch. Biochem. Biophys. 1988, 264, 321
39. Haidle, A. M.; Myers, A. G. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 12048
40. Thilly, W. G.; Liber, H. L.; Wogan, G. N. Front. Biol. 1978, 46, 53
41. Linghan, R. B.; Hsu, A.; Silverman, K. C.; Bills, G. F.; Dombrowski, A.; Goldman, M. E.; Darke, P. L.; Huang, L.; Koch, G.; Ondeyka, J. G.; Goetz, M. A. J. Antibiot. 1992, 45, 686
42. Shen, R.; Zhu, S.; Huang, X. J. Org. Chem. 2009, 74, 4118
43. Huang, X.; Zhu, S.; Shen, R. Adv. Synth. Catal. 2009, 351, 3118
44. Shen, R.; Chen, L.; Huang, X. Adv. Synth. Catal. 2009, 351, 2833
45. Black, D. A.; Arndtsen, B. A. Org. Lett. 2004, 6, 1107
46. Deutsch, E. A.; Snider, B. B. J. Org. Chem. 1982, 47, 2682
47. Deutsch, E. A.; Snider, B. B. Tetrahedron Lett. 1983, 24, 3701
48. Keck, G. E.; Kachensky, D. F. J. Org. Chem. 1986, 51, 2487
49. Gibbs, R. A.; Bartels, K.; Lee, R. W. K.; Okamura, W. H. J. Am. Chem. Soc. 1989, 111, 3717
50. Curtin, M. L.; Okamura, W. H. J. Org. Chem. 1990, 55, 5278
51. Krause, N. Liebigs Ann. Chem. 1993, 521
52. int = 0.0149), number of observations [ I > 2σ(I)] 2749, parameters 292. Supplementary crystallographic data have been deposited at the Cambridge Crystallographic Data Centre, CCDC 793327.
53. int = 0.0337), number of observations [ I > 2σ(I)] 2405, parameters 210. Supplementary crystallographic data have been deposited at the Cambridge Crystallographic Data Centre, CCDC 793326.
54. int = 0.0320), number of observations [ I > 2σ(I)] 1893, parameters 263. Supplementary crystallographic data have been deposited at the Cambridge Crystallographic Data Centre, CCDC 793328.