Chiral zinc(II) and copper(II)-catalyzed asymmetric ring-opening reactions of meso-epoxides with aniline and indole derivatives

Tetrahedron

Volumn 66, Issue 5, 2010, Pages 1111-1118

  Kokubo, Masaya ^a   Naito, Takeshi ^a   Kobayashi, Shu ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ANILINE DERIVATIVE; COPPER; DICHLOROMETHANE; EPOXIDE; INDOLE DERIVATIVE; LIGAND; SCANDIUM; SURFACTANT; ZINC;

ARTICLE; ASYMMETRIC CATALYSIS; CATALYST; CHIRALITY; CRYSTAL STRUCTURE; ENANTIOMER; ENANTIOSELECTIVITY; PRIORITY JOURNAL; QUANTUM YIELD; REACTION ANALYSIS; RING OPENING;

EID: 73349095396     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.11.018     Document Type: Article

References (54)

1. In: Cornils B., and Herrmann W.A. (Eds). Aqueous-Phase Organometallic Catalysis. 2nd ed. (2004), Wiley-VCH, Weinheim
2. Kobayashi S. Pure Appl. Chem. 79 (2007) 235
3. Li C.-J., and Chan T.-H. Organic Reactions in Aqueous Media (1997), John Wiley, New York, NY
4. In: Grieco P.A. (Ed). Organic Synthesis in Water (1998), Blackie Academic and Professional, London
5. Ishikawa S., Hamada T., Manabe K., and Kobayashi S. J. Am. Chem. Soc. 126 (2004) 12236
6. Kobayashi S., Ogino T., Shimizu H., Ishikawa S., Hamada T., and Manabe K. Org. Lett. 7 (2005) 4729
7. Kobayashi S., and Wakabayashi T. Tetrahedron Lett. 39 (1998) 5389
8. Manabe K., Mori Y., Wakabayashi T., Nagayama S., and Kobayashi S. J. Am. Chem. Soc. 122 (2000) 7202
9. Manabe K., Sun X.-M., and Kobayashi S. J. Am. Chem. Soc. 123 (2001) 10101
10. Manabe K., Iimura S., Sun X.-M., and Kobayashi S. J. Am. Chem. Soc. 124 (2002) 11971
11. Kokubo M., Ogawa C., and Kobayashi S. Angew. Chem., Int. Ed. 47 (2008) 6909
12. Nugent W.A. J. Am. Chem. Soc. 114 (1992) 2768
13. Martinez L.E., Leighton J.L., Carsten D.H., and Jacobsen E.N. J. Am. Chem. Soc. 117 (1995) 5897
14. Hou X.-L., Wu J., Dai L.-X., Xia L.-J., and Tang M.-H. Tetrahedron: Asymmetry 9 (1998) 1747
15. Sagawa S., Abe H., Hase Y., and Inada T. J. Org. Chem. 64 (1999) 4962
16. Sekine A., Ohshima T., and Shibasaki M. Tetrahedron 58 (2002) 75
17. Azoulay S., Manabe K., and Kobayashi S. Org. Lett. 7 (2005) 4593
18. Ogawa C., Azoulay S., and Kobayashi S. Heterocycles 66 (2005) 201
19. Carree F., Gli R., and Collin J. Org. Lett. 7 (2005) 1023
20. Kureshy R.I., Singh S., Khan N.H., Abdi S.H.R., Suresh E., and Jasra R.V. Eur. J. Org. Chem. (2006) 1303
21. Arai K., Salter M.M., Yamashita Y., and Kobayashi S. Angew. Chem., Int. Ed. 46 (2007) 955
22. Mai E., and Schneider C. Synlett (2007) 2136
23. Ogawa C., Wang N., Boudou M., Azoulay S., Manabe K., and Kobayashi S. Heterocycles 72 (2007) 589
24. Jacobsen E.N., Kakiuchi F., Konsler R.G., Larrow J.F., and Tokunaga M. Tetrahedron Lett. 38 (1997) 773
25. Matsunaga S., Das J., Roels J., Vogl E.M., Yamamoto N., Iida T., Yamaguchi K., and Shibasaki M. J. Am. Chem. Soc. 122 (2000) 2252
26. Tschöp A., Marx A., Sreekanth A.R., and Schneider C. Eur. J. Org. Chem. (2007) 2318
27. Cole B.M., Shimizu K.D., Krueger C.A., Harrity J.P.A., Snapper M.L., and Hoveyda A.H. Angew. Chem., Int. Ed. 35 (1996) 1668
28. Shimizu K.D., Cole B.M., Krueger C.A., Kuntz K.W., Snapper M.L., and Hoveyda A.H. Angew. Chem., Int. Ed. 36 (1997) 1704
29. Schaus S.E., and Jacobsen E.N. Org. Lett. 2 (2000) 1001
30. Zhu C., Yuan F., Gu W., and Pan Y. Chem. Commun. (2003) 692
31. Iida T., Yamamoto N., Sasai H., and Shibasaki M. J. Am. Chem. Soc. 119 (1997) 4783
32. Wu M.H., and Jacobsen E.N. J. Org. Chem. 63 (1998) 5252
33. Wu J., Hou X.L., Dai L.X., Xia L.J., and Tang M.H. Tetrahedron: Asymmetry 9 (1998) 3431
34. Boudou M., Ogawa C., and Kobayashi S. Adv. Synth. Catal. 348 (2006) 2585
35. Ogawa C., Wang N., and Kobayashi S. Chem. Lett. 36 (2007) 34
36. Chen Y.-J., and Chen C. Tetrahedron: Asymmetry 18 (2007) 1313
37. Nugent W.A. J. Am. Chem. Soc. 120 (1998) 7139
38. Denmark S.E., Barsanti P.A., Wong K.T., and Stavenger R.A. J. Org. Chem. 63 (1998) 2428
39. Tao B., Lo M.M.C., and Fu G.C. J. Am. Chem. Soc. 123 (2001) 353
40. Nakaijama M., Saito M., Uemura M., and Hashimoto S. Tetrahedron Lett. 43 (2002) 8827
41. Tokuoka E., Kotani S., Matsunaga H., Ishizuka T., Hashimoto S., and Nakaijama M. Tetrahedron: Asymmetry 16 (2005) 2391
42. Tschöp A., Nandakumar M.V., Pavlyuk O., and Schneider C. Tetrahedron Lett. 49 (2008) 1030
43. Tiecco M., Testaferri L., Marini F., Sternativo S., Verme F.D., Santi C., Bagnoli L., and Temperini A. Tetrahedron 64 (2008) 3337
44. Katrizky A.R., and Pozharskii A.F. Handbook of Heterocyclic Chemistry. 2nd ed. (2002), Pergamon, Oxford
45. Austin J.F., and MacMillan D.W.C. J. Am. Chem. Soc. 124 (2002) 1172
46. Ishikawa S., Hamada T., Manabe K., and Jobayashi S. Synlett (2005) 2716
47. For the preparation of cis-alkenes:
48. Bellucci G., Chiappe C., and Lo Moro G. Tetrahedron Lett. 37 (1996) 4225
49. Creary X. Org. Synth. 7 (1986) 438
50. Ravi Shankar B.K., and Shechter H. Tetrahedron Lett. 23 (1982) 2277
51. Bosanac T., and Wilcox C.S. Org. Lett. 6 (2004) 2321
52. For the preparation of meso-epoxides:. Lusinchi X., and Hanquet G. Tetrahedron 53 (1997) 13727
53. Arai K., Lucarini S., Salter M.M., Ohta K., Yamashita Y., and Kobayashi S. J. Am. Chem. Soc. 129 (2007) 8103
54. Mai E., and Schneider C. Chem.-Eur. J. 13 (2007) 2729