Dirhodium(II) Tetrakis[alkyl 2-oxaazetidine-4(S)-carboxylates]. A New Set of Effective Chiral Catalysts for Asymmetric Intermolecular Cyclopropanation Reactions with Diazoacetates

Synlett

Volumn 1996, Issue 7, 1996, Pages 697-698

  Doyle, Michael P ^a   Zhou, Qi Lin ^a   Simonsen, Stanley H ^b   Lynch, Vincent ^b  

^a TRINITY UNIVERSITY   (United States)

^b UNIVERSITY OF TEXAS AT AUSTIN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002330507     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5573     Document Type: Article

References (20)

1. 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.
2. Doyle, M. P.; Kalinin, A. V. J. Org. Chem. 1996, 61, 2179.
3. Martin, S. F.; Oalmann, C. J.; Liras, S. Tetrahedron Lett. 1992, 33, 6727.
4. Doyle, M. P.; Eismont, M. Y.; Protopopova, M. N.; Kwan, M. M. Y. Tetrahedron 1994, 50, 1665.
5. Doyle, M. P.; Winchester, W. R.; Hoorn, J. A. A.; Lynch, V.; Simonsen, S. H.; Ghosh, R. J. Am. Chem. Soc. 1993, 115, 9968.
6. Doyle, M. P.; Zhou, Q.-L.; Dyatkin, A. B.; Ruppar, D. A. Tetrahedron Lett. 1995, 36, 7579.
7. Doyle, M. P.; Dyatkin, A. B.; Protopopova, M. N.; Yang, C. I.; Miertschin, C. S.; Winchester, W. R. Rec. Trav. Chim. Pays-Bas 1995, 114, 163.
8. Doyle, M. P.; Zhou, Q.-L. Tetrahedron: Asymmetry 1995, 6, 2157.
9. (a) Pfaltz, A. Acc. Chem Res. 1993, 2 6, 339.
10. (b) Leutenegger, U.; Umbricht, G.; Fahrni, C.; von Matt, P.; Pfaltz, A. Tetrahedron 1992, 48, 2143.
11. Evans, D. A.; Woerpel, K. A.; Hinman, M. M.; Faul, M. M. J. Am. Chem. Soc. 1991, 113, 726.
12. Lowenthal, R. E.; Abiko, A.; Masamune, S. Tetrahedron Lett. 1990, 31, 6005.
13. Lowenthal, R. E.; Masamune, S. Tetrahedron Lett. 1991, 32, 7373.
14. (a) Müller, P.; Baud, C.; Ene, D.; Motallebi, S.; Doyle, M. P.; Brandes, B. D.; Dyatkin, A. B.; See, M. M. Helv. Chim. Acta 1995, 78, 459.
15. (b) Doyle, M. P.; Winchester, W. R.; Protopopova, M. N.; Müller, P.; Bernardinelli, G.; Ene, D.; Motallebi, S. Helv. Chim. Acta 1993, 76, 2227.
16. Zervas, L.; Winitz, M.; Greenstein, J. P. J. Org. Chem. 1957, 22, 1515.
17. Salzmann, T. N.; Ratcliffe, R. W.; Christensen, B. G.; Bouffard, F. A. J. Am. Chem. Soc. 1980, 102, 6161.
18. 23 = -327 (c 0.70, MeCN).
19. O'Malley, S.; Kodadek, T. Organometal. 1992, 11, 2299.
20. Pfaltz has reported (ref. 9a) 97% ee for both 4t and 4c from 2e, but the diastereomer ratio was 63:37 (4t:4c).