Chiral catalysts for enantioselective intermolecular cyclopropanation reactions with methyl phenyldiazoacetate. Origin of the solvent effect in reactions catalyzed by homochiral dirhodium(II) prolinates

Tetrahedron Letters

Volumn 37, Issue 24, 1996, Pages 4129-4132

  Doyle, Michael P ^a   Zhou, Qi Lin ^a   Charnsangavej, Chutaporn ^a   Longoria, Mario A ^a   McKervey, M Anthony ^b   García, Concepción Fernandez ^b  

^a TRINITY UNIVERSITY   (United States)

^b QUEEN'S UNIVERSITY BELFAST   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID DERIVATIVE; CYCLOPROPANE DERIVATIVE; LIGAND; PENTANE; PROLINE DERIVATIVE; RHODIUM DERIVATIVE; SOLVENT;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHIRALITY; ENANTIOMER; MOLECULAR INTERACTION; STEREOCHEMISTRY;

EID: 0029941742     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00822-2     Document Type: Article

References (22)

1. (a) Ye, T.; McKervey, M. A. Chem. Rev. 1994, 94, 1091.
2. (b) Doyle, M. P. In Comprehensive Organometallic Chemistry II, Vol. 12; Hegedus, L. S., Ed.; Pergamon Press: New York, 1995; Ch. 5.1.
3. (c) Reissig, H.-U. In Stereoselective Synthesis of Houben-Weyl Methods of Organic Chemistry, Vol. E21c; Helmchen, G.; Hoffmann, R. W.; Mulzer, J.; Schaumann, E., Eds.; Georg Thieme Verlag: New York, 1995; Section 1.6.1.5.
4. Aratani, T. Pure & Appl. Chem. 1985, 57, 1839.
5. Pfaltz, A. Acc. Chem. Res. 1993, 26, 339.
6. (a) Lowenthal, R. E.; Abiko, A.; Masamune, S. Tetrahedron Lett. 1990, 31, 6005.
7. (b) Evans, D. A.; Woerpel, K. A.; Hinman, M. M. J. Am. Chem. Soc. 1991, 113, 726.
8. (c) Muller, D.; Umbricht, G.; Weber, B.; Pfaltz, A. Helv. Chim. Acta 1991, 74, 232.
9. Nishiyama, H.; Itoh, Y.; Sugawara, Y.; Matsumoto, H.; Aoki, K.; Itoh, K. Bull. Chem. Soc. Jpn. 1995, 68, 1247.
10. Doyle, M. P.; Bagheri, V.; Wandless, T. J.; Harn, N. K.; Brinker, D. A.; Eagle, C. T.; Loh, K.-L. J. Am. Chem. Soc. 1990, 112, 1906.
11. Doyle, M. P. In Catalytic Asymmetric Synthesis; Ojima, I. Ed.; VCH Publishers: New York, 1993, Ch. 3.
12. Doyle, M. P.; Zhou, Q.-L. Tetrahedron: Asymmetry 1995, 6, 2157.
13. (a) Davies, H. M. L.; Hutcheson, D. K. Tetrahedron Lett. 1993, 34, 7243.
14. (b) Davies, H. M. L.; Peng, Z.-Q.; Houser, J. H. Tetrahedron Lett. 1994, 35, 8939.
15. Corey, E. J.; Grant, T. G. Tetrahedron Lett. 1994, 35, 5373.
16. Kennedy, M.; McKervey, M. A.; Maguire, A. R.; Roos, G. H. P. J. Am. Chem. Soc., Chem. Commun. 1990, 361.
17. Doyle, M. P.; Winchester, W. R.; Hoorn, J. A. A.; Lynch, V.; Simonsen, S. H.; Ghosh, R. J. Am. Chem. Soc. 1993, 115, 9967.
18. Doyle, M. P.; Winchester, W. R.; Protopopova, M. N.; Müller, P.; Bernardinelli, G.; Ene, D.; Motallebi, S. Helv. Chim. Acta 1993, 76, 2227.
19. Doyle, M. P.; Dyatkin, A. B.; Protopopova, M. N.; Yang, C. I.; Miertschin, C. S.; Winchester, W. R.; Simonsen, S. H.; Lynch, V.; Ghosh, R. Recl. Trav. Chim. Pays-Bas 1995, 114, 163.
20. McKervey, M. A.; Ye, T. J. Chem. Soc., Chem. Commun. 1992, 823.
21. Hashimoto, S.; Watanabe, N.; Sato, T.; Shiro, M.; Ikegami, S. Tetrahedron Lett. 1993, 34, 5109.
22. 3).