Highly efficient and enantioselective cyclopropanation of styrene with diazoacetates using a new copper-(Schiff-base) catalyst

Tetrahedron Asymmetry

Volumn 11, Issue 5, 1999, Pages 1157-1163

  Li, Zhengning ^a   Zheng, Zhuo ^a   Chen, Huilin ^a  

^a DALIAN INSTITUTE OF CHEMICAL PHYSICS   (China)

Author keywords

[No Author keywords available]

Indexed keywords

2 AMINO 1,1 DI(3,5 DI TERT BUTYLPHENYL)PROPANOL; 5 NITROSALICYLALDEHYDE; COPPER ACETATE; COPPER COMPLEX; CYCLOPROPANE; DIAZOACETATE; REAGENT; SCHIFF BASE; STYRENE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHEMICAL REACTION; CONTROLLED STUDY; ENANTIOMER; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 0344002698     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(00)00037-9     Document Type: Article

References (38)

1. (a) Singh, V. K.; Gupta, A. D.; Sekar, G. Synthesis 1997, 137.
2. (b) Doyle, M. P. In Catalytic Asymmetric Synthesis; Ojima, I. Ed.; VCH: New York, 1993.
3. (c) Doyle, M. P.; Protopopova, M. N. Tetrahedron 1998, 54, 7919.
4. (a) Aratani, T.; Yoneyoshi, Y.; Nagase, T. Tetrahedron Lett. 1975, 1707.
5. (b) Aratani, T.; Yoneyoshi, Y.; Nagase, T. Tetrahedron Lett. 1977, 2599.
6. (c) Aratani, T.; Yoneyoshi, Y.; Nagase, T. Tetrahedron Lett. 1982, 23, 685.
7. (d) Aratani, T. Pure Appl. Chem. 1985, 57, 1839.
8. Nakamura, A.; Honishi, A.; Tatsuno, Y.; Otsuka, S. J. Am. Chem. Soc. 1978, 100, 3443.
9. (a) Fritschi, H.; Leutenegger, U.; Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1986, 25, 1005.
10. (b) Pfaltz, A. Acc. Chem. Res. 1993, 26, 339.
11. (a) Lowenthal, R. E.; Abiko, A.; Masamune, S. Tetrahedron Lett. 1990, 31, 6005.
12. (b) Evans, D. A.; Woerpel, K. A.; Hinman, M. M.; Faul, M. M. J. Am. Chem. Soc. 1991, 113, 726.
13. (c) Lowenthal, R. E.; Masamune, S. Tetrahedron Lett. 1991, 32, 7373.
14. (d) Muller, D.; Umbricht, G.; Weber, B.; Pfaltz, A. Helv. Chim. Acta 1991, 74, 232.
15. (e) Uozumi, Y.; Kyota, H.; Kishi, E.; Kitayama, K.; Hayashi, T. Tetrahedron: Asymmetry 1996, 7, 1603.
16. (f) Bedekar, A. V.; Koroleva, E. B.; Andersson, P. G. J. Org. Chem. 1997, 62, 2518.
17. (a) Ito, K.; Katsuki, T. Tetrahedron Lett. 1993, 34, 2661.
18. (b) Ito, K.; Yoshitake, M.; Katsuki, T. Heterocycles 1996, 42, 305.
19. (a) Nishiyama, H.; Itoh, H.; Matsumoto, H.; Park, S.-B.; Itoh, K. J. Am. Chem. Soc. 1994, 116, 2223.
20. (b) Nishiyama, H.; Itoh, Y.; Sugawara, Y.; Matsumoto, H.; Aoki, K.; Itoh, K. Bull. Chem. Soc. Jpn. 1995, 68, 1247.
21. (a) Doyle, M. P.; Brandes, B. D.; Kazala, A. P.; Pieters, R. J.; Jarstfer, M. B.; Watkins, L. M.; Eagle, C. T. Tetrahedron Lett. 1990, 31, 6613.
22. (b) Davies, H. M. L.; Bruzinski, P. R.; Lake, D. H.; Kong, N.; Fall, M. J. J. Am. Chem. Soc. 1996, 118, 6897.
23. (a) Lo, M. M.-C.; Fu, G. C. J. Am. Chem. Soc. 1998, 120, 10270.
24. (b) Tanner, D.; Johansson, F.; Harden, A.; Andersson, P. G. Tetrahedron 1998, 54, 15 731.
25. (a) Gross, Z.; Galili, N.; Simkhovich, L. Tetrahedron Lett. 1999, 40, 1571.
26. (b) Frauenkron, M.; Berkessel, A. Tetrahedron Lett. 1997, 38, 7175.
27. (c) Lo, W.-C.; Che, C.-M.; Cheng, K.-F.; Mak, T. C. W. Chem. Commun. 1997, 1205.
28. Nozaki, H.; Moriuti, S.; Takaya, H.; Noyori, R. Tetrahedron Lett. 1966, 5239.
29. Fukuda, T.; Katsuki, T. Tetrahedron 1997, 53, 7201.
30. Yamada, T.; Ikeno, T.; Sekino, H.; Sato, M. Chem. Lett. 1999, 719.
31. (a) Brunner, H.; Miehling, W. Monatsh. Chem. 1984, 115, 1237.
32. (b) Liu, S.; Chen, F. Chem. J. Chin. Univ. 1998, 19, 568.
33. (c) Raza, Z.; Dokovic, S.; Vinkovic, V.; Sunjic, V. Croatica Chem. Acta 1996, 69, 1545.
34. Cai, L.; Mahmoud, H.; Han, Y. Tetrahedron: Asymmetry 1999, 10, 411.
35. Sawamura, M.; Ito, Y. Chem. Rev. 1992, 92, 857.
36. Li, Z.; Chen, H.; Guo, H. Chin. J. Mol. Catal. 1992, 6, 352.
37. Li, Z.; Chen, H. Chin. J. Chem. Lett. 1996, 7, 785.
38. Hill, P.; Robinson, R. J. Chem. Soc. 1933, 486.