Monomeric Rhodium(II) Catalysts for the Preparation of Aziridines and Enantioselective Formation of Cyclopropanes from Ethyl Diazoacetate at Room Temperature

Journal of Organic Chemistry

Volumn 68, Issue 25, 2003, Pages 9705-9710

  Krumper, J R ^a,b   Gerisch, M ^a,b   Suh, J M ^a,b   Bergman, R G ^a,b   Tilley, T D ^a,b  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b LAWRENCE BERKELEY NATIONAL LABORATORY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPROPANATION;

CATALYST ACTIVITY; CATALYSTS; ISOMERS; MONOMERS; OLEFINS; RHODIUM; THERMAL EFFECTS;

AMINES;

ALKENE; AZIRIDINE; CYCLOPROPANE; DIAZOACETIC ACID ETHYL ESTER; IMINE; MONOMER; RHODIUM DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL STRUCTURE; CIS ISOMER; COMPLEX FORMATION; CYCLOPROPANATION; ENANTIOMER; ENANTIOSELECTIVITY; REACTION ANALYSIS; ROOM TEMPERATURE; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0344235360     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo035120e     Document Type: Article

References (49)

1. Ojima, I., Ed. Catalytic Asymmetric Synthesis, 2nd ed.; Wiley-VCH: New York, 2000.
2. Sweeney, J. B. Chem. Soc. Rev. 2002, 31, 247.
3. Doyle, M. P. Chem. Rev. 1986, 86, 919.
4. Singh, V. K.; DattaGupta, A.; Sekar, G. Synthesis 1997, 137.
5. Doyle, M. P.; Forbes, D. C. Chem. Rev. 1998, 98, 911.
6. Doyle, M. P.; Protopopova, M. N. Tetrahedron 1998, 54, 7919.
7. Doyle, M. P.; Peterson, C. S.; Zhou, Q. L.; Nishiyama, H. Chem. Commun. 1997, 211.
8. Fritschi, H.; Leutenegger, U.; Pfaltz, A. Helv. Chim. Acta 1988, 71, 1553.
9. Lowenthal, R. E.; Abiko, A.; Masamune, S. Tetrahedron Lett. 1990, 31, 6005.
10. Nishiyama, H.; Itoh, Y.; Matsumoto, H.; Park, S.-B.; Itoh, K. J. Am. Chem. Soc. 1994, 116, 2223.
11. Nishiyama, H.; Itoh, Y.; Sugawara, Y.; Matsumoto, H.; Aoki, K.; Itoh, K. Bull. Chem. Soc. Jpn. 1995, 68, 1247.
12. Miller, J. A.; Jin, W.; Nguyen, S. T. Angew. Chem., Int. Ed. 2002, 41, 2953.
13. Loffler, F.; Hagen, M.; Luning, U. Synlett 1999, 1826.
14. Werle, T.; Maas, G. Adv. Synth. Catal. 2001, 343, 37.
15. Diaz-Requejo, M. M.; Belderraín, T. R.; Trofimenko, S.; Pérez, P. J. J. Am. Chem. Soc. 2001, 123, 3167.
16. Diaz-Requejo, M. M.; Caballero, A.; Belderrain, T. R.; Nicasio, M. C.; Trofimenko, S.; Perez, P. J. J. Am. Chem. Soc. 2002, 124, 978.
17. Doyle, M. P.; Winchester, W. R.; Protopopova, M.; Muller, P.; Bernadinelli, G.; Ene, D.; Motallebi, S. Helv. Chim. Acta 1993, 76, 2227.
18. Doyle, M. P.; Zhou, Q. L.; Simonsen, S. H.; Lynch, V. Synlett 1996, 697.
19. Uchida, T.; Irie, R.; Katsuki, T. Synlett 1999, 11, 1793.
20. Doyle, M. P.; Davies, S. B.; Hu, W. H. Chem. Commun. 2000, 867.
21. Niimi, T.; Uchida, T.; Irie, R.; Katsuki, T. Adv. Synth. Catal. 2001, 343.
22. Tanner, D. Angew. Chem., Int. Ed. Engl. 1994, 33, 599.
23. Osborn, H. M. I.; Sweeney, J. B. Tetrahedron: Asymmetry 1997, 8, 1693.
24. Hansen, K. B.; Finney, N. S.; Jacobsen, E. N. Angew. Chem., Int. Ed. Engl. 1995, 34, 676.
25. Aggarwal, V. K.; Thompson, A.; Jones, R. V. H.; Standen, M. C. H. J. Org. Chem. 1996, 61, 8368.
26. Antilla, J. C.; Wulff, W. D. J. Am. Chem. Soc. 1999, 121, 5099.
27. Aggarwal, V. K.; Ferrara, M. Org. Lett. 2000, 2, 4107.
28. Antilla, J. C.; Wulff, W. D. Angew. Chem., Int. Ed. 2000, 39, 4518.
29. Aggarwal, V. K.; Alonso, E.; Fang, G.; Ferrara, M.; Hynd, G.; Porcelloni, M. Angew. Chem., Int. Ed. 2001, 40, 1433.
30. Gerisch, M.; Krumper, J. R.; Bergman, R. G.; Tilley, T. D. J. Am. Chem. Soc. 2001, 123, 5818.
31. Gerisch, M.; Krumper, J. R.; Bergman, R. G.; Tilley, T. D. Organometallics 2003, 22, 47.
32. Bedekar, A. V.; Koroleva, E. B.; Andersson, P. G. J. Org. Chem. 1997, 62, 2518.
33. Pandey, K. K. Coord. Chem. Rev. 1992, 121, 1.
34. DeWitt, D. G. Coord. Chem. Rev. 1996, 147, 209.
35. Davies, H. M. L. Eur. J. Org. Chem. 1999, 2459.
36. Davies, H. M. L.; Panaro, S. A. Tetrahedron 2000, 56, 4871.
37. Eagle, C. T.; Farrar, D. G.; Pfaff, C. U.; Davies, J. A.; Kluwe, C.; Miller, L. Organometallics 1998, 17, 4523.
38. Doyle, M. P.; Winchester, W. R.; Hoorn, J. A. A.; Lynch, V.; Simonsen, S. H.; Ghosh, R. J. Am. Chem. Soc. 1993, 115, 9968.
39. Shankar, B. K. R.; Shechter, H. Tetrahedron Lett. 1982, 23, 2277.
40. Dias, E. L.; Brookhart, M.; White, P. S. Chem. Commun. 2001, 423.
41. Casarrubios, L.; Perez, J. A.; Brookhart, M.; Templeton, J. L. J. Org. Chem. 1996, 61, 8358.
42. Gunnoe, T. B.; White, P. S.; Templeton, J. L.; Casarrubios, L. J. Am. Chem. Soc. 1997, 119, 3171.
43. Rasmussen, K. G.; Jorgensen, K. A. J. Chem. Soc., Perkin Trans. 1 1997, 1287.
44. Mohan, J. M.; Uphade, B. S.; Choudhary, V. R.; Ravindranathan, T.; Sudalai, A. Chem. Commun. 1997, 1429.
45. Rasmussen, K. G.; Hazell, R. G.; Jorgensen, K. A. Acta Chem. Scand. 1998, 52, 1056.
46. Kubo, T.; Sakaguchi, S.; Ishii, Y. Chem. Commun. 2000, 625.
47. Doyle, M. P.; Hu, W. H.; Timmons, D. J. Org. Lett. 2001, 3, 933.
48. Morales, D.; Perez, J.; Riera, L.; Riera, V.; Corzo-Suarez, R.; Garcia-Granda, S.; Miguel, D. Organometallics 2002, 21, 1540.
49. Wolf, J. R.; Hamaker, C. G.; Djukic, J.-P.; Kodadek, T.; Woo, L. K. J. Am. Chem. Soc. 1995, 117, 9194.