Novel structure-defined chiral bis(oxazolinyl)thiophenes for Ru-catalyzed asymmetric cyclopropanation

Tetrahedron Letters

Volumn 45, Issue 29, 2004, Pages 5649-5652

  Gao, Ming Z ^a   Kong, Deyuan ^a   Clearfield, Abraham ^a   Zingaro, Ralph A ^a  

^a TEXAS A AND M UNIVERSITY   (United States)

Author keywords

Asymmetric cyclopropanation; Bis(oxazoline); Bis(oxazolinyl)thiophene; Ruthenium

Indexed keywords

BENZENE DERIVATIVE; ESTER DERIVATIVE; OXAZOLINE DERIVATIVE; RUTHENIUM;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHIRALITY; CYCLOPROPANATION; ENANTIOSELECTIVITY; X RAY ANALYSIS; X RAY DIFFRACTION;

EID: 3042618792     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.05.120     Document Type: Article

References (32)

1. Meier W. Chem. Soc. Rev. 29:2000;295
2. Suckling C.J. Angew. Chem., Int. Ed. Engl. 27:1988;537
3. Nozaki H., Moriuti S., Takaya H., Noyori R. Tetrahedron Lett. 7:1966;5239
4. Nozaki H., Takaya H., Moriuti S., Noyori R. Tetrahedron. 24:1968;3655
5. Fritschi H., Leutenegger U., Pfaltz A. Angew. Chem., Int. Ed. Engl. 25:1986;1005
6. Doyle M.P., Protopopova M.N. Tetrahedron. 54:1998;7919
7. Doyle M.P., Forbes D.C. Chem. Rev. 98:1998;911
8. Lebel H., Marcoux J.-F., Molinaro C., Charette A.B. Chem. Rev. 103:2003;977
9. Aratani T., Yoneyoshi Y., Nagase T. Tetrahedron Lett. 16:1975;1707
10. Aratani T., Yoneyoshi Y., Nagase T. Tetrahedron Lett. 23:1982;685
11. Fukuda T., Katsuki T. Tetrahedron. 53:1997;7201
12. Ikeno T., Sato M., Yamada T. Chem. Lett. 1999;1345
13. Davies H.M.L., Bruzinski P.R., Lake D.H., Kong N., Fall M.J. J. Am. Chem. Soc. 118:1996;6897
14. Lo W.-C., Che C.-M., Cheng K.-F., Mark T.C.W. J. Chem. Soc., Chem. Commun. 1997;1205
15. Zhang J.-L., Che C.-M. Org. Lett. 4:2002;1911
16. Ghosh A.K., Mathivanan P., Cappiello J. Tetrahedron: Asymmetry. 9:1998;1
17. Gao M.Z., Wang B. Prog. Chem. 14(5):2002;347
18. Evans D.A., Woerpel K.A., Hinman M.M., Faul M.M. J. Am. Chem. Soc. 113:1991;726
19. Nishiyama H., Itoh Y., Matsumoto H., Park S.-B., Itoh K. J. Am. Chem. Soc. 116:1994;2223
20. Nishiyama H., Itoh Y., Sugawara Y., Matsumoto H., Aoki K., Itoh K. Bull. Chem. Soc. Jpn. 68:1995;1247
21. Gupta A.D., Bhuniya D., Singh V.K. Tetrahedron. 50:1994;13725
22. Uozurui Y., Kyota H., Kishi E., Kitayama K., Hoyashi T. Tetrahedron: Asymmmetry. 7:1996;1603
23. Benincori T., Brenna E., Sannicolò F., Trimarco L., Antognazza P., Cesarotti E., Demartin F., Pilati T. J. Org. Chem. 61:1996;6244
24. Voituriez A., Schulz E. Tetrahedron: Asymmetry. 14:2003;339
25. Gao M.Z., Wang B., Liu H.B., Xu Z.L. Chin. J. Chem. 20(1):2002;85
26. 2S: C, 64.64; H, 7.83; N, 8.37; S, 9.58. Found: C, 64.97; H, 8.08; N, 8.14; S, 9.13
27. Evans D.A., Scheidt K.A., Fandrick K.R., Lam H.W., Wu J. J. Am. Chem. Soc. 125:2003;10780
28. Boulch R., Scheurer A., Mosset P., Saalfrank R.W. Tetrahedron Lett. 41:2000;1023
29. Kim S.-G., Cho C.-W., Ahn K.H. Tetrahedron: Asymmetry. 8:1997;1023
30. Glos M., Reiser O. Org. Lett. 2:2000;2045
31. Sheldrick, G. M.; SHELXTL, version 5.03; Siemens Analytical X-ray Instruments: Madison, WI, 1995
32. Sheldrick, G. M.; SHELX-96 Program for Crystal Structure Determination; Bruker-AXS: Madison, WI, 1996