Synthesis of novel chiral bisoxazoline ligands containing 2,5-diaryl-1,3,4-oxadiazole and enantioselective cyclopropanation of styrene

Synthesis

Volumn , Issue 16, 2002, Pages 2347-2352

  Du, Da Ming ^a   Wang, Zhan Yue ^a   Xu, Dong Cheng ^a   Hua, Wen Ting ^a  

^a Peking University   (China)

Author keywords

Bisoxazoline; Enantioselective cyclopropanation; Oxadiazole

Indexed keywords

CATALYSTS; SYNTHESIS (CHEMICAL);

LIGANDS;

ORGANIC COMPOUNDS;

1,3,4 OXADIAZOLE DERIVATIVE; 2 PHENYLCYCLOPROPANECARBOXYLATE; 2,5 BIS(2 CARBOXYLPHENYL) 1,3,4 OXADIAZOLE; 2,5 DIPHENYL 1,3,4 OXADIAZOLE; AMINOALCOHOL; BISOXAZOLINE DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; COPPER COMPLEX; DIAZOACETIC ACID ETHYL ESTER; LIGAND; METHANESULFONYL CHLORIDE; OXAZOLINE DERIVATIVE; STYRENE; TOLUENESULFONYL CHLORIDE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHEMICAL REACTION; CHIRALITY; COMPLEX FORMATION; CYCLIZATION; CYCLOPROPANATION; ENANTIOSELECTIVITY; REACTION ANALYSIS; SYNTHESIS;

EID: 0036441847     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2002-35232     Document Type: Article

References (39)

1. Visiting scholar of Wenzhou Medical College, Wenzhou 325003, Zhejiang P.R.China.
2. (a) Ghosh, A. K.; Mathivanan, P.; Cappiello, J. Tetrahedron: Asymmetry 1998, 9, 1.
3. (b) Johnson, J. S.; Evans, D. A. Acc. Chem. Res. 2000, 33, 325.
4. (a) Nishiyama, H.; Sakaguchi, H.: Nakamura, T.; Horiharta, M.; Itoh, K. Organometallics 1989, 8, 846.
5. (b) Nishiyama, H.; Kondo, M.; Nakamura, T.; Itoh, K. Organometallics 1991, 10, 500.
6. (c) Imai, Y.; Zhang, W.; Kida, T.; Nakatsuji, Y.; Ikeda, I. Tetrahedron: Asymmetry 1996, 7, 2453.
7. (a) Leutenegger, U.; Umbricht, G.; Fahrni, C.; von Matt, P.; Pfaltz, A. Tetrahedron 1992, 48, 2143.
8. (b) Pfaltz, A. Acc. Chem. Res. 1993, 26, 339.
9. Ji, J.; Barnes, D. M.; Zhang, J.; King, S. A.; Wittenberger, S. J.; Morton, H. E. J. Am. Chem. Soc. 1999, 121, 10215.
10. (a) Corey, E. J.; Imai, N.; Zhang, H. Y. J. Am. Chem. Soc. 1991, 113, 728.
11. (b) Evans, D. A.; Murry, J. A.; von Mat, P.; Norcross, R. D.; Miller, S. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 798.
12. (c) Ghosh, A. K.; Cho, H.; Cappiello, J. Tetrahedron: Asymmetry 1998, 9, 3687.
13. (a) Evans, D. A.; Woerpel, K. A.; Scott, M. J. Angew. Chem., Int. Ed. Engl. 1992, 31, 430.
14. (b) Gant, T. G.; Noe, M. C.; Corey, E. J. Tetrahedron Lett. 1995, 36, 8745.
15. (c) Kim, S. G.; Cho, C. W.; Ahn, K. H. Tetrahedron: Asymmetry 1997, 8, 1023.
16. (a) Wu, H. C.; Xu, D. C.; Hua, W. T. Acta Chim. Sinica 2001, 59, 1340.
17. (b) Wang, Z. Y.; Du, D. M.; Wu, D.; Hua, W. T. Synth. Commun. 2002, 32, in press.
18. (a) Seki, H.; Koga, K; Matsuo, H.; Ohki, S.; Matsuo, I. I.; Yamada, S. Chem. Pharm. Bull. 1965, 13, 995.
19. (b) Stanfield, C. F.; Parker, J. E.; Kanellis, P. J. Org. Chem. 1981, 46, 4799.
20. (c) Giannis, A.; Sandhoff, K Angew. Chem, Int. Ed. Engl. 1989, 28, 218.
21. (d) Mckennon, M. J.; Meyers, A. I.; Drauz, K.; Schwarm, M. J. Org. Chem. 1993, 58, 3568.
22. (a) Reuman, M.; Meyers, A. I. Tetrahedron 1985, 41, 837.
23. (b) Breton, P.: Andre-Barres, C.; Langlois, Y. Synth. Commun. 1992, 22, 2543.
24. (c) Jones, R. C. F.; Ward, G. J. Tetrahedron Lett. 1988, 29, 3853.
25. (d) Gant, T. G.; Meyers, A. I. Tetrahedron 1994, 50, 2297.
26. (a) Vorbrüggen, H.; Krolikiewicz, K. Tetrahedron Lett. 1981, 22, 4471.
27. (b) Vorbrüggen, H.; Krolikiewicz, K. Tetrahedron 1993, 49, 9353.
28. Denmark, S. E.; Nakajima, N.; Nicaise O. J. C.; Faucher, A. M.; Edwards, J. P. J. Org. Chem. 1995, 60, 4884.
29. Peer, M.; de Jong, J. C.; Kiefer, M.; Langer, T.; Rieck, H.; Schell, H.; Sennhenn, P.: Sprinz, J.; Steinhagen, H.; Wiese, B.; Helmchen, G. Tetrahedron 1996, 52, 7547.
30. Aratani, T.; Nakanisi, Y.; Nozaki, H. Tetrahedron 1970, 26, 1675.
31. Uchida, T.; Irie, R.; Katsuki, T. Synlett 1999, 1793.
32. Boulch, R.; Scheurer, A.; Mosset, P.; Saalfrank, R. W. Tetrahedron Lett. 2000, 41, 1023.
33. Uchida, T.; Irie, R.; Katsuki, T. Tetrahedron 2000, 56, 3501.
34. Alexander, K.; Cook, S.; Gibsona, C. L. Tetrahedron Lett. 2000, 41, 7135.
35. Crystallographic data (excluding structure factors) for the structures in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication numbers CCDC 182921 & 182922 Copies of the data can be obtained free of charge on application to CCDC 12 Union Road Cambridge CB2 1EZ UK [fax:+44(1223)336033 or e-mail: deposit@ccdc.cam.ac.uk].
36. (a) Preson, J. J. Heterocycl. Chem. 1965, 2, 441.
37. (b) Zhou, J. M.; Hua, W. T.; Yang, Q. C. Chem. J. Chinese Universities-Chinese 1996, 17, 1721.
38. Sheldrick, G. M. SHELXS-97 Program for the Solution of Crystal Structures; University of Goettingen: Germany, 1997.
39. Sheldrick, G. M. SHELXL-97 Program for the Refinement of Crystal Structures; University of Goettingen: Germany, 1997.