Highly enantioselective intramolecular cyclopropanation reactions of N-Allylic-N-methyldiazoacetamides catalyzed by chiral dirhodium(II) carboxamidates

Journal of Organic Chemistry

Volumn 61, Issue 6, 1996, Pages 2179-2184

  Doyle, Michael P ^a   Kalinin, Alexey V ^a  

^a TRINITY UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DIAZO DECOMPOSITION; DIRHODIUM; ENANTIOCONTROL; ENANTIOSELECTIVE; IMIDAZOLIDIN; INTRAMOLECULAR CYCLOPROPANATIONS; INTRAMOLECULAR DIPOLAR CYCLOADDITION; TETRAKIS;

CARBOXYLATION; CYCLOADDITION; ENANTIOSELECTIVITY; RHODIUM;

CATALYSIS;

EID: 0001030980     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9519219     Document Type: Article

References (22)

1. Doyle, M. P.; Eismont, M. Y.; Protopopova, M. N.; Kwan, M. M. Y. Tetrahedron 1994, 50, 1665.
2. (a) Sturm, H.; Ongania, K.-H.; Daly, J. J.; Klötzer, W. Chem. Ber. 1981, 114, 190.
3. (b) Minami, T.; Kamitamari, M.; Utsunomiya, T.; Tanaka, T.; Ichikawa, J. Bull. Chem. Soc. Jpn. 1993, 66, 1496.
4. (a) Regitz, M.; Mass, G. Aliphatic Diazo Compounds-Properties and Synthesis; Academic Press: New York, 1986.
5. (b) Challis, B. C.; Latif, F. J. Chem. Soc., Perkin Trans. 1 1990, 1005.
6. Doyle, M. P.; Austin, R. E.; Bailey, A. S.; Dwyer, M. P.; Dyatkin, A. B.; Kalinin, A. V.; Kwan, M. M. Y.; Liras, S.; Oalmann, C. J.; Pieters, R. J.; Protopopova, M. N.; Raab, C. E.; Roos, G. H. P.; Zhou, Q.-L.; Martin, S. F. J. Am. Chem. Soc. 1995, 117, 5763.
7. Nordlander, J. E.; Catalane, D. B.; Eberline, T. H.; Farkas, L. V.; Howe, R. S.; Stevens, R. M.; Tripoulas, N. A. Tetrahedron Lett. 1978, 4987.
8. Quihia, A.; René, L.; Guilhem, J.; Pascard, C.; Badet, B. J. Org. Chem. 1993, 58, 1641.
9. Doyle, M. P.; Pieters, R. J.; Taunton, J.; Pho, H. Q.; Padwa, A.; Hertzog, D. L.; Precedo, L. J. Org. Chem. 1991, 56, 820.
10. Doyle, M. P.; Winchester, W. R.; Hoorn, J. A. A.; Lynch, V.; Simonsen, S. H.; Ghosh, R. J. Am. Chem. Soc. 1993, 115, 9968.
11. 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.
12. Doyle, M. P.; Dyatkin, A. B.; Roos, G. H. P.; Cañas, F.; Pierson, D. A.; Basten, A. van; Müller, P.; Polleux, P. J. Am. Chem. Soc. 1994, 116, 4507.
13. Doyle, M. P.; Protopopova, M. N.; Zhou, Q.-L.; Bode, J. W.; Simonsen, S. H.; Lynch, V. J. Org. Chem. 1995, 60, 6654.
14. Doyle, M. P.; Westrum, L. J.; Wolthuis, W. N. E.; See, M. M.; Boone, W. P.; Bagheri, V.; Pearson, M. M. J. Am. Chem. Soc. 1993, 115, 958.
15. Doyle, M. P.; Dorow, R. L.; Tamblyn, W. H. J. Org. Chem. 1982, 47, 4059.
16. Similar processes, including the well-known "apparent" allylic C-H insertion, have been previously observed: (a) Alonso, M. E.; Fernandez, R. Tetrahedron 1989, 45, 3313.
17. (b) Doyle, M. P. Chem. Rev. 1986, 89, 919.
18. Doyle, M. P.; Zhou, Q.-L.; Dyatkin, A. B.; Ruppar, D. A. Tetrahedron Lett. 1995, 36, 7579.
19. Blankley, J.; Sauter, F. J.; House, H. O. Organic Syntheses; Wiley: New York, 1973; Collect. Vol. V, p 259.
20. Grigoryan, D. V.; Kazaryan, A. T.; Martirosyan, G. T.; Babayan, A. T. Zh. Org. Khim. 1971, 6, 1390.
21. Deshpande, R. S.; Tipnis, H. P.; Kulkarni, V. M. Indian J. Chem., Sect. B 1976, 14B, 979.
22. Voshchula, V. N.; Tolkunov, S. V.; Zubritskii, M. Yu.; Dulenko, V. I. Chem. Heterocycl. Compds. 1988, 24, 1175.