N -heterocyclic carbene (NHC)-catalyzed highly diastereo- and enantioselective oxo-Diels-Alder reactions for synthesis of fused pyrano[2,3- b ]indoles

Organic Letters

Volumn 14, Issue 11, 2012, Pages 2894-2897

  Yang, Limin ^a,b   Wang, Fei ^a,b   Chua, Pei Juan ^b   Lv, Yunbo ^b   Zhong, Liang Jun ^a   Zhong, Guofu ^a  

^a HANGZHOU NORMAL UNIVERSITY   (China)

^b Nanyang Technological University   (Singapore)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; CARBENE; DRUG DERIVATIVE; FUSED HETEROCYCLIC RINGS; INDOLE DERIVATIVE; METHANE; PYRONE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; STEREOISOMERISM; SYNTHESIS;

ALDEHYDES; CATALYSIS; CYCLIZATION; HETEROCYCLIC COMPOUNDS, 3-RING; INDOLES; METHANE; MOLECULAR STRUCTURE; PYRONES; STEREOISOMERISM;

EID: 84861820257     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol301175z     Document Type: Article

References (48)

1. Bourissou, D.; Guerret, O.; Gabbai, F. P.; Bertrand, G. Chem. Rev. 2000, 100, 39-91
2. Herrmann, W. A.; Weskamp, T.; Bohm, V. P. W. Adv. Organomet. Chem. 2001, 48, 1-69
3. Herrmann, W. A. Angew. Chem., Int. Ed. 2002, 41, 1290-1309
4. Scott, N. M.; Nolan, S. P. Eur. J. Inorg. Chem. 2005, 44, 1815-1828
5. Seebach, D. Angew. Chem., Int. Ed. 1979, 18, 239-258
6. Enders, D.; Niemeier, O.; Henseler, A. Chem. Rev. 2007, 107, 5606-5655
7. Moore, J. L.; Rovis, T. Top. Curr. Chem. 2010, 291, 77-144
8. Marion, N.; Díez-González, S.; Nolan, S. P. Angew. Chem., Int. Ed. 2007, 46, 2988-3000
9. He, M.; Struble, J. R.; Bode, J. W. J. Am. Chem. Soc. 2006, 128, 8418-8420
10. He, M.; Uc, G. J.; Bode, J. W. J. Am. Chem. Soc. 2006, 128, 15088-15089
11. Struble, J. R.; Kaeobamrung, J.; Bode, J. W. Org. Lett. 2008, 10, 957-960
12. He, M.; Beahm, B. J.; Bode, J. W. Org. Lett. 2008, 10, 3817-3820
13. Breslow, R. J. Am. Chem. Soc. 1958, 80, 3719-3726
14. Sheehan, J.; Hunneman, D. H. J. Am. Chem. Soc. 1966, 88, 3666-3667
15. Enders, D.; Breuer, K. Comprehensive Asymmetric Catalysis; Springer-Verlag: Heidelberg, Germany, 1999; Vol. 3, pp 1093-1102.
16. Stetter, H. Angew. Chem., Int. Ed. 1976, 15, 639-647
17. Enders, D. Stereoselective Synthesis; Springer-Verlag: Heidelberg, Germany, 1993; pp 63-90.
18. Enders, D.; Breuer, K.; Runsink, J.; Teles, J. H. Helv. Chim. Acta 1996, 79, 1899-1902
19. Yang, L.; Tan, B.; Wang, F.; Zhong, G. J. Org. Chem. 2009, 74, 1744-1746
20. Sohn, S. S.; Rosen, E. L.; Bode, J. W. J. Am. Chem. Soc. 2004, 126, 14370-14371
21. Burstein, C.; Glorius, F. Angew. Chem., Int. Ed. 2004, 43, 6205-6208
22. He, M.; Bode, J. W. Org. Lett. 2005, 7, 3131-3134
23. Chan, A.; Scheidt, K. A. J. Am. Chem. Soc. 2007, 129, 5334-5335
24. Phillips, E. M.; Reynolds, T. E.; Scheidt, K. A. J. Am. Chem. Soc. 2008, 130, 2416-2417
25. Kaeobamrung, J.; Kozlowski, M. C.; Bode, J. W. Proc. Natl. Acad. Sci. U.S.A. 2010, 107, 20661-20665
26. Yang, L.; Wang, F.; Lee, R.; Lv, Y.; Huang, K.-W.; Zhong, G. Submitted.
27. Zhang, Y.-R.; Lv, H.; Zhou, D.; Ye, S. Chem.-Eur. J. 2008, 14, 8473-8476
28. Kobayashi, S.; Kinoshita, T.; Uehara, H.; Sudo, T.; Ryu, I. Org. Lett. 2009, 11, 3934-3937
29. Fang, X.; Chen, X.; Chi, Y. R. Org. Lett. 2011, 13, 4708-4711
30. Ling, K. B.; Smith, A. D. Chem. Commun. 2011, 47, 373-375
31. Das, B.; Laxminarayana, K.; Krishnaiah, M.; Kumar, D. N. Bioorg. Med. Chem. Lett. 2009, 22, 6396-6398
32. Kasaplar, P.; Yilmazer, O.; Cagir, A. Bioorg. Med. Chem. 2009, 1, 311-314
33. Hamilton, H. W.; Tait, B. D.; Gajda, C.; Hagen, S. E.; Ferguson, D.; Lunney, E. A.; Pavlovsky, A.; Tummino, P. J. Bioorg. Med. Chem. Lett. 1996, 6, 719-724
34. Dewick, P. M. Medicinal Natural Products: A Biosynthetic Approach, 2 nd ed.; Wiley: New York, 2002; pp 189200.
35. Gataullin, R. R. J. Org. Chem. 2008, 45, 321-354
36. Ohnuma, T.; Kasuya, H.; Kimura, Y.; Ban, Y. Heterocycles 1982, 17, 377-380
37. Nakagawa, M.; Sodeoka, M.; Yamaguchi, K.; Hino, T. Chem. Pharm. Bull. 1984, 32, 1373-1384
38. Fritz, H.; Losacker, P. Justus Liebigs Ann. Chem. 1967, 709, 135-150
39. Feldman, K. S.; Karatjas, A. G. Org. Lett. 2004, 6, 2849-2852
40. Kam, T. S.; Tan, S. J.; Ng, S. W.; Komiyama, K. Org. Lett. 2008, 10, 3749-3752
41. Reh, S.; Bergman, J. Tetrahedron 2005, 61, 3115-3123
42. Lv, H.; Chen, X.-Y.; Sun, L.-H.; Ye, S. J. Org. Chem. 2010, 75, 6973-6976
43. For review of the chemistry of N -mesityl catalysts, see: Chiang, P.-C.; Bode, J. W. TCI MAIL 2011, 149, 2-17
44. For their syntheses, see: Struble, J. R.; Bode, J. W. Org. Synth. 2010, 87, 362-376
45. For mechanistic studies, see: Mahatthananchai, J.; Bode, J. W. Chem. Sci. 2012, 3, 192-197
46. Long, D. R.; Richards, C. G.; Ross, M. S. F. J. Hetereocycl. Chem. 1978, 15, 633-636
47. Autrey, R. L.; Tahk, F. C. Tetrahedron 1967, 23, 901-917
48. Jones, G.; Rae, W. J. Tetrahedron 1966, 22, 3021-3026