Novel axially chiral bis-arylthiourea-based organocatalysts for asymmetric Friedel-Crafts type reactions

Tetrahedron Letters

Volumn 47, Issue 39, 2006, Pages 7037-7042

  Fleming, Eimear M ^a   McCabe, Thomas ^a   Connon, Stephen J ^a  

^a TRINITY COLLEGE DUBLIN   (Ireland)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; INDOLE DERIVATIVE; THIOUREA DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHIRALITY; ENANTIOSELECTIVITY; FRIEDEL CRAFTS REACTION;

EID: 33747762352     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.07.112     Document Type: Article

References (51)

1. Friedel C., and Crafts J.M. C.R. Hebd. Seances Acad. Sci. 84 (1877) 1392
2. Friedel C., and Crafts J.M. C.R. Hebd. Seances Acad. Sci. 84 (1877) 1450
3. Olah G.A. Friedel-Crafts Chemistry (1973), Wiley, New York
4. Reviews:. Bandini M., Melloni A., Tommasi S., and Umani-Ronchi A. Synlett (2005) 1199
5. Bandini M., Melloni A., and Umani-Ronchi A. Angew. Chem., Int. Ed. 43 (2004) 550
6. Jørgensen K.A. Synthesis (2003) 1117
7. Jensen K.B., Thorbauge J., Hazell R.G., and Jørgensen K.A. Angew. Chem., Int. Ed. 40 (2001) 160
8. Zhuang W., Hansen T., and Jørgensen K.A. Chem. Commun. (2001) 347
9. Zhou J., and Tang Y. J. Am. Chem. Soc. 124 (2002) 9030
10. Evans D.A., Scheidt K.A., Fandrick K.R., Lam H.W., and Wu J. J. Am. Chem. Soc. 125 (2003) 10780
11. Zhou J., Ye M.-C., Huang Z.-Z., and Tang Y. J. Org. Chem. 69 (2004) 1309
12. Zhou J., and Tang Y. Chem. Commun. (2004) 432
13. Palomo C., Oiarbide M., Kardak B.G., Garcia J.M., and Linden A. J. Am. Chem. Soc. 127 (2005) 4154
14. Yamazaki S., and Iwata Y. J. Org. Chem. 71 (2006) 739
15. Jia Y.-X., Zhu S.-F., Yang Y., and Zhou Q.-L. J. Org. Chem. 71 (2006) 75
16. Bandini M., Fagioli M., Melchiorre P., Melloni A., and Umani-Ronchi A. Tetrahedron Lett. 44 (2003) 5843
17. Paras N.A., and MacMillan D.W.C. J. Am. Chem. Soc. 123 (2001) 4370
18. Austin J.F., and MacMillan D.W.C. J. Am. Chem. Soc. 124 (2002) 1172
19. Noland W.E., and Lange R.F. J. Am. Chem. Soc. 81 (1959) 1203
20. For examples of asymmetric organocatalytic addition reactions to nitroolefins using thioureas see:. Okino T., Hoashi Y., and Takemoto Y. J. Am. Chem. Soc. 125 (2003) 12672
21. Okino T., Hoashi Y., Furukawa T., Xu X., and Takemoto Y. J. Am. Chem. Soc. 127 (2005) 119
22. McCooey S.H., and Connon S.J. Angew. Chem., Int. Ed. 44 (2005) 6367
23. Ye J., Dixon D.J., and Hynes P.S. Chem. Commun. (2005) 4481
24. Reviews:. Connon S.J. Chem. Eur. J. 12 (2006) 5418
25. Taylor M.S., and Jacobsen E.N. Angew. Chem., Int. Ed. 45 (2006) 1520
26. Takemoto Y. Org. Biomol. Chem. 3 (2005) 4299
27. Pihko P.M. Angew. Chem., Int. Ed. 43 (2004) 2062
28. Schreiner P.R. Chem. Soc. Rev. 32 (2003) 289
29. Dessole G., Herrera R.P., and Ricci A. Synlett (2004) 2374
30. Herrera R.P., Sgarzani V., Bernardi L., and Ricci A. Angew. Chem., Int. Ed. 44 (2005) 6576
31. Zhuang W., Hazell R.G., and Jørgensen K.A. Org. Biomol. Chem. 3 (2005) 2566
32. Maher D.J., and Connon S.J. Tetrahedron Lett. 45 (2004) 1301
33. Wittkopp A., and Schreiner P.R. Chem. Eur. J. 9 (2003) 407
34. For the use of bis-N-arylthioureas in other catalytic processes see:. Curran D.P., and Kuo L.H. J. Org. Chem. 59 (1994) 3259
35. Curran D.P., and Kuo L.H. Tetrahedron Lett. 36 (1995) 6647
36. Schreiner P.R., and Wittkopp A. Org. Lett. 4 (2002) 217
37. Okino T., Hoashi Y., and Takemoto Y. Tetrahedron Lett. 44 (2003) 2817
38. Hoashi Y., Yabuta T., and Takemoto Y. Tetrahedron Lett. 45 (2004) 9185
39. For discussion, see Ref. 21.
40. Thiourea catalysts for asymmetric Pictet-Spengler reactions which do not incorporate N-aryl substituents:. Taylor M.S., and Jacobsen E.N. J. Am. Chem. Soc. 126 (2004) 10558
41. 3 as the optimal solvent in these catalysed reactions.
42. Thadani A.N., Stankovic A.R., and Rawal V.H. Proc. Natl. Acad. Sci. U.S.A. 101 (2004) 5846
43. Crystallographic data for 13 have been deposited with the Cambridge Crystallographic Data Centre, deposit number CCDC609063.
44. 1H NMR spectrum of 13.
45. For examples of the demonstrable s-cis,cis conformational preference of thioureas see:. Tel R.M., and Engberts J.B.F.N. J. Chem. Soc., Perkin Trans. 2 (1976) 483
46. Etter M.C., and Panunto T.W. J. Am. Chem. Soc. 110 (1988) 5896
47. Etter M.C., Urbañczyk-Lipkowska Z., Zia-Ebrahimi M., and Panunto T.W. J. Am. Chem. Soc. 112 (1990) 8415
48. Vachal P., and Jacobsen E.N. J. Am. Chem. Soc. 124 (2002) 10012
49. Okino T., Hoashi Y., Furukawa T., Xu X., and Takemoto Y. J. Am. Chem. Soc. 127 (2005) 119
50. The X-ray crystal structure of cyclohexyl-substituted urea-based catalyst 8 exhibited an s-cis,cis urea conformation. The distance between the urea hydrogen atoms is 2.12 Å.
51. + requires 849.0992. Found 849.1013.