Chiral brønsted acid catalyzed stereoselective [3+3] cycloaddition reaction of azomethine ylide to vinylimine intermediates: constructing fully functionalized chiral tetrahydro-β-carboline

Acta Chimica Sinica

Volumn 71, Issue 6, 2013, Pages 879-883

  Huang, Jianzhou ^a   Luo, Shiwei ^a   Gong, Liuzhu ^a  

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

Author keywords

3+3 cycloaddition; Asymmetric catalysis; Azomethine ylide; Chiral phosphoric acid; Tetrahydro carboline

Indexed keywords

EID: 84880451348     PISSN: 05677351     EISSN: None     Source Type: Journal    
DOI: 10.6023/A13020217     Document Type: Article

References (51)

1. Hollinshead S. P, Trudell M. L, Skolnick P, Cook J. M. J. Med. Chem. 1990 33(3) 1062;
2. Garnier J, Mahuteau J, Plat M, Merienne C. Phytochemistry 1989 28(1) 308;
3. Itoh A, Tanahashi T, Nagakura N, Nishi T. Phytochemistry 2003 62(3) 359;
4. Bentley K. W. Nat. Prod. Rep. 2004 21(3) 395.
5. Taylor M. S, Jacobsen E. N. J. Am. Chem. Soc. 2004 126(34) 10558;
6. Seayad J, Seayad A. M, List B. J. Am. Chem. Soc. 2006 128(4) 1086;
7. Raheem I. T, Thiara P. S, Peterson E. A, Jacobsen E. N. J. Am. Chem. Soc. 2007 129(44) 13404;
8. Wanner M. J, van der Haas R. N. S, de Cuba K. R, van Maarseveen J. H, Hiemstra H. Angew. Chem. Int. Ed. 2007 46(39) 7485;
9. Bou-Hamdan F. R, Leighton J. L. Angew. Chem. Int. Ed. 2009 48(13) 2403;
10. Muratore M. E, Holloway C. A, Pilling A. W, Storer R. I, Trevitt G, Dixon D. J. J. Am. Chem. Soc. 2009 131(31) 10796.
11. Agnusdei M, Bandini M, Melloni A, Umani-Ronchi A. J. Org. Chem. 2003 68(18) 7126;
12. Bandini M, Melloni A, Piccinelli F, Sinisi R, Tommasi S, Umani-Ronchi A. J. Am. Chem. Soc. 2006 128(5) 1424;
13. Li C.-F, Liu H, Liao J, Cao Y.-J, Liu X.-P, Xiao W.-J. Org. Lett. 2007 9(10) 1847;
14. Rannoux C, Roussi F, Retailleau P, Guéritte F. O. Org. Lett. 2010 12(6) 1240;
15. Zhang Y.-Q, Zhu D.-Y, Jiao Z.-W, Li B.-S, Zhang F.-M, Tu Y.-Q, Bi Z. Org. Lett. 2011 13(13) 3458.
16. Kogan N. A, Kul'bitskii G. N. Chem. Heterocycl. Compd. 1978 14 46.
17. For a review: Palmieri A, Petrini M, Shaikh R. R. Org. Biomol. Chem. 2010 8(6) 1259.
18. Cozzi P. G, Benfatti F, Zoli L. Angew. Chem. Int. Ed. 2009 48(7) 1313;
19. Han B, Xiao Y.-C, Yao Y, Chen Y.-C. Angew. Chem. Int. Ed. 2010 49 10189;
20. Wang D.-S, Tang J, Zhou Y.-G, Chen M.-W, Yu C.-B, Duan Y, Jiang G.-F. Chem. Sci. 2011 2(4) 803;
21. Xiao J, Zhao K, Loh T.-P. Chem. Asian. J. 2011 6(11) 2890;
22. Xiao J. Org. Lett. 2012 14(7) 1716;
23. Xu B, Guo Z.-L, Jin W.-Y, Wang Z.-P, Peng Y.-G, Guo Q.-X. Angew. Chem. Int. Ed. 2012 51(4) 1059.
24. Guo Q.-X, Peng Y.-G, Zhang J.-W, Song L, Feng Z, Gong L.-Z. Org. Lett. 2009 11(20) 4620;
25. Guo C, Song J, Huang J.-Z, Chen P.-H, Luo S.-W, Gong L.-Z. Angew. Chem. Int. Ed. 2012 51(4) 1046.
26. Addition reaction of vinylimine intermediates under basic condition see: Ballini R, Palmieri A, Petrini M, Torregiani E. Org. Lett. 2006 8(18) 4093;
27. Palmieri A, Petrini M. J. Org. Chem. 2007 72(5) 1863.
28. Han X, Li H, Hughes R. P, Wu J. Angew. Chem. Int. Ed. 2012 51(41) 10390;
29. Xiao Y.-C, Zhou Q.-Q, Dong L, Liu T.-Y, Chen Y.-C. Org. Lett. 2012 14(23) 5940;
30. Wang L, Xie X, Liu Y.-H. Org. Lett. 2012 14(23) 5848.
31. For reviews see: Dömling A. Chem. Rev. 2005 106(1) 17;
32. Ramón D. J, Yus M. Angew. Chem. Int. Ed. 2005 44(11) 1602;
33. Ramachary D. B, Jain S. Org. Biomol. Chem. 2011 9(5) 1277;
34. van Berkel S. S, Bogels B. G. M, Wijdeven M. A, Westermann B, Rutjes F. Eur. J. Org. Chem. 2012 (19) 3543;
35. de Graaff C, Ruijter E, Orru R. V. A. Chem. Soc. Rev. 2012 41(10) 3969.
36. Wu X, Dai X, Fang H, Nie L, Chen J, Cao W, Zhao G. Chem. Eur. J. 2011 17(38) 10510;
37. Ausmees K, Kriis K, Pehk T, Werner F, Järving I, Lopp M, Kanger T. J. Org. Chem. 2012 77(23) 10680;
38. Marson C. M. Chem. Soc. Rev. 2012 41(23) 7712;
39. Pellissier H. Adv. Synth. Catal. 2012 354(2-3) 237;
40. Su Y, Bouma M. J, Alcaraz L, Stocks M, Furber M, Masson G, Zhu J. Chem. Eur. J. 2012 18(40) 12624;
41. Xie X, Peng C, He G, Leng H.-J, Wang B, Huang W, Han B. Chem. Commun. 2012 48(85) 10487;
42. He R, Zeng L.-F, He Y, Wu L, Michelle Gunawan A, Zhang Z.-Y. Chem. Commun. 2013 49(20) 2064;
43. Li X, Zhao Y, Qu H, Mao Z, Lin X. Chem. Commun. 2013 49(14) 1401.
44. For review see: Yu J, Shi F, Gong L.-Z. Acc. Chem. Res. 2011 44(11) 1156;
45. Wu X, Gong L.-Z. Acta Chim. Sinica DOI: 10.6023/A13030279.
46. Chen X.-H, Zhang W.-Q, Gong L.-Z. J. Am. Chem. Soc. 2008 130(17) 5652;
47. Chen X.-H, Wei Q, Luo S.-W, Xiao H, Gong L.-Z. J. Am. Chem. Soc. 2009 131(38) 13819;
48. Yu J, He L, Chen X.-H, Song J, Chen W.-J, Gong L.-Z. Org. Lett. 2009 11(21) 4946;
49. Wang C, Chen X.-H, Zhou S.-M, Gong L.-Z. Chem. Commun. 2010 46(8) 1275;
50. He L, Chen X.-H, Wang D.-N, Luo S.-W, Zhang W.-Q, Yu J, Ren L, Gong L.-Z. J. Am. Chem. Soc. 2011 133(34) 13504.
51. CCDC 926838 for compound 4f. See the Supporting Information for Details.