Rational tuning of the rigidity of a ligand scaffold: synthesis of diphenylsulfide-linked bis(oxazoline) ligands and their application in asymmetric allylic alkylation

Tetrahedron Asymmetry

Volumn 21, Issue 2, 2010, Pages 241-246

  Du, Xian ^a   Liu, Han ^b   Du, Da Ming ^a  

^a BEIJING INSTITUTE OF TECHNOLOGY   (China)

^b PEKING UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

BIS(OXAZOLINE); LIGAND; OXAZOLINE DERIVATIVE; PALLADIUM; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; ASYMMETRIC ALLYLIC ALKYLATION; ASYMMETRIC SYNTHESIS; CATALYSIS; CATALYST; ENANTIOSELECTIVITY; PRIORITY JOURNAL; RIGIDITY; SUBSTITUTION REACTION;

EID: 77949541229     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2010.01.015     Document Type: Article

References (55)

1. Jacobsen E.N., Pfaltz A., and Yamamoto H. Comprehensive Asymmetric Catalysis Vols. 1-3 (1999), Springer, Berlin
2. Ojima I. Catalytic Asymmetric Synthesis. 2nd ed. (2000), Wiley-VCH, New York
3. Mikami K., and Lautens M. New Frontiers in Asymmetric Catalysis (2007), Wiley & Sons, Hoboken
4. For reviews, see:. Ghosh A.K., Mathivanan P., and Cappiello J. Tetrahedron: Asymmetry 9 (1998) 1
5. Gómez M., Muller G., and Rocamora M. Coord. Chem. Rev. 193-195 (1999) 769
6. Jørgensen K.A., Johannsen M., Yao S., Audrain H., and Thorhauge J. Acc. Chem. Res. 32 (1999) 605
7. Rechavi D., and Lemaire M. Chem. Rev. 102 (2002) 3467
8. McManus H.A., and Guiry P.J. Chem. Rev. 104 (2004) 4151
9. Rasappan R., Laventine D., and Reiser O. Coord. Chem. Rev. 252 (2008) 702
10. Hargaden G.C., and Guiry P.J. Chem. Rev. 109 (2009) 2505
11. For reviews, see:. Johnson J.S., and Evans D.A. Acc. Chem. Res. 33 (2000) 325
12. Desimoni G., Faita G., and Quadrelli P. Chem. Rev. 103 (2003) 3119
13. Desimoni G., Faita G., and Jørgensen K.A. Chem. Rev. 106 (2006) 3561
14. Nishiyama H. Chem. Soc. Rev. 36 (2007) 1133
15. For review, see:. Flanagan S.P., and Guiry P.J. J. Organomet. Chem. 691 (2006) 2125
16. For recent examples, see:. Jacobsen E.N., Zhang W., and Guler M.L. J. Am. Chem. Soc. 113 (1991) 6703
17. Nishiyama H., Yamaguchi S., Kondo M., and Itoh K. J. Org. Chem. 57 (1992) 4306
18. RajanBabu T.V., Ayers T.A., and Casalnuovo A.L. J. Am. Chem. Soc. 116 (1994) 4101
19. Park S.-B., Murata K., Matsumoto H., and Nishiyama H. Tetrahedron: Asymmetry 6 (1995) 2487
20. Belda O., Kaiser N.-F., Bremberg U., Larhed M., Hallberg A., and Moberg C. J. Org. Chem. 65 (2000) 5868
21. Aubel P.G., Khokhar S.S., Driessen W.L., Challa G., and Reedijk J. J. Mol. Catal. A: Chem. 175 (2001) 27
22. Jew S.-S., Yoo M.-S., Jeong B.-S., and Park I.Y. Org. Lett. 4 (2002) 4245
23. McGarrigle E.M., Murphy D.M., and Gilheany D.G. Tetrahedron: Asymmetry 15 (2004) 1343
24. Fu Y., Hou G.-H., Xie J.-H., Xing L., Wang L.-X., and Zhou Q.-L. J. Org. Chem. 69 (2004) 8157
25. Okino K., Hoashi Y., Furukawa T., Xu X., and Takemoto Y. J. Am. Chem. Soc. 127 (2005) 119
26. Liu H., and Xu J. J. Mol. Catal. A: Chem. 244 (2006) 68
27. Yan X.X., Peng Q., Zhang Y., Zhang K., Hong W., Hou X.-L., and Wu Y.-D. Angew. Chem. Int. Ed. 45 (2006) 1979
28. Yan X.X., Peng Q., Li Q., Zhang K., Yao J., Hou X.-L., and Wu Y.-D. J. Am. Chem. Soc. 130 (2008) 14362
29. For recent examples, see:. Fang T., Xu J., and Du D.-M. Lett. Org. Chem. 3 (2006) 780
30. Liu H., Li W., and Du D.-M. Sci. China, Ser. B 52 (2009) 1321
31. Trost B.M., and Strege P.E. J. Am. Chem. Soc. 99 (1977) 1649
32. For recent reviews, see:. Trost B.M., and van Vranken D.M. Chem. Rev. 96 (1996) 395
33. Trost B.M., and Crawley M.L. Chem. Rev. 103 (2003) 2921
34. Lu Z., and Ma S. Angew. Chem., Int. Ed. 47 (2008) 258
35. For selected reports, see:. Weix D.J., and Hartwig J.F. J. Am. Chem. Soc. 129 (2007) 7720
36. Liu D., Xie F., and Zhang W. Tetrahedron Lett. 48 (2007) 7591
37. Zhao X., Liu D., Xie F., and Zhang W. Tetrahedron 65 (2009) 512
38. Trost B.M., and Zhang Y. J. Am. Chem. Soc. 129 (2007) 14548
39. Gómez M., Jansat S., Muller G., Maestro M.A., and Mahía J. Organometallics 21 (2002) 1077
40. Voituriez A., and Schulz E. Tetrahedron: Asymmetry 14 (2003) 339
41. Voituriez A., Fiaud J.-C., and Schulz E. Tetrahedron Lett. 43 (2002) 4907
42. Lu S.-F., Du D.-M., Zhang S.-W., and Xu J. Tetrahedron: Asymmetry 15 (2004) 3433
43. Du D.-M., Lu S.-F., Fang T., and Xu J. J. Org. Chem. 70 (2005) 3712
44. Lu S.-F., Du D.-M., Xu J., and Zhang S.-W. J. Am. Chem. Soc. 128 (2006) 7418
45. Lu S.-F., Du D.-M., and Xu J. Org. Lett. 8 (2006) 2115
46. Liu H., Xu J., and Du D.-M. Org. Lett. 9 (2007) 4725
47. Liu H., Lu S.-F., Xu J., and Du D.-M. Chem. Asian J. 3 (2008) 1111
48. 2 has been reported:. Kooijman H., Spek A.L., Zondervan C., and Feringa B.L. Acta Crystallogr., Sect. E 58 (2002) m429
49. Eldin S., and Jencks W.P. J. Am. Chem. Soc. 117 (1995) 4851
50. Rabai J. Synthesis (1989) 523
51. Kinoshita N., Kawabata T., Tsubaki K., Bando M., and Fuji K. Tetrahedron 62 (2006) 1756
52. Nagy P., Csámpai A., Szabó D., Varga J., Harmat V., Ruff F., and Kucsman A. J. Chem. Soc., Perkin Trans. (2001) 339
53. Dieter H. Chem. Ber. 120 (1987) 1151
54. Tanaka Y., Mino T., Akita K., Sakamoto M., and Fujita T. J. Org. Chem. 69 (2004) 6679
55. Polet D., Alexakis A., Tissot-Croset K., Corminboeuf C., and Ditrich K. Chem. Eur. J. 12 (2006) 3596