Vinyldiazolactone as a vinylcarbene precursor: Highly selective C-H insertion and cyclopropanation reactions

Journal of the American Chemical Society

Volumn 128, Issue 50, 2006, Pages 16038-16039

  Bykowski, Darren ^a   Wu, Kou Hui ^a   Doyle, Michael P ^a  

^a Bldg 142   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBENOID; LACTONE DERIVATIVE; RHODIUM DERIVATIVE; VINYLDIAZOLACTONE;

ARTICLE; CATALYST; CHEMICAL REACTION; CYCLOPROPANATION; SYNTHESIS;

ALKENES; CARBON; CATALYSIS; CYCLIZATION; HYDROGEN; LACTONES; MOLECULAR STRUCTURE; PROPANE; VINYL COMPOUNDS;

EID: 33845576373     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja066452e     Document Type: Article

References (26)

1. (a) Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds: From Cyclopropanes to Ylides; Wiley: New York, 1998; p 652.
2. (b) Davies, H. M. L.; Walji, A. M. Modern Rhodium-Catalyzed Organic Reactions; Evans, P. A., Ed.: Wiley-VCH: Weinheim, Germany, 2005; p 301.
3. (a) Davies, H. M. L.; Dai, X.; Long, M. S. J. Am. Chem. Soc. 2006, 128, 2485.
4. (b) Nyong, A. M.; Rainier, J. D. J. Org. Chem. 2005, 70, 746.
5. (c) Yan, M.; Jacobsen, N.; Hu, W.; Gronenberg Luisa, S.; Doyle, M. P.; Colyer John, T.; Bykowski, D. Angew. Chem., Int. Ed. 2004, 43, 6713.
6. (d) Doyle. M. P.; Yan, M.; Hu, W.; Gronenberg, L. S. J. Am. Chem. Soc. 2003, 125, 4692.
7. (e) Davies, H. M. L.; Stafford, D. G.; Hansen, T. Org. Lett. 1999, 1, 233.
8. (f) Davies, H. M. L.; Doan, B. D. J. Org. Chem. 1998, 63, 657.
9. Davies, H. M. L.; Huby, N. J. S.; Cantrell, W. R., Jr.; Olive, J. L. J. Am. Chem. Soc. 1993, 115, 9468.
10. Davies, H. M. L.; Hodges, L. M.; Matasi, J. J.; Hansen, T.; Stafford, D. G. Tetrahedron Lett. 1998, 39, 4417.
11. (a) Bulugahapitiya, P.; Landais, Y.; Parra-Rapado, L.; Planchenault, D.; Weber, V. J. Org. Chem. 1997, 62, 1630.
12. (b) Landais, Y.; Planchenault, D.; Weber. V. Tetrahedron Lett. 1994, 35, 9549.
13. Baum, J. S.; Shook, D. A.; Davies, H. M. L.; Smith, H. D. Synth. Commun. 1987, 17, 1709.
14. (a) Davies, H. M. L.; Beckwith, R. E. J. Chem. Rev. 2003, 103, 2861.
15. (b) Davies, H. M. L.; Antoulinakis, E. G. J. Organomet. Chem. 2001, 617-618, 47.
16. Davies, H. M. L. Eur. J. Org. Chem. 1999, 2459.
17. Doyle, M. P.; Van Oeveren, A.; Westrum, L. J.; Protopopova, M. N.; Clayton, T. W., Jr. J. Am. Chem. Soc. 1991, 113, 8982.
18. Doyle, M. P.; Davies, S. B.; Hu, W. Org. Lett. 2000, 2, 1145.
19. Hu, W.; Timmons, D. J.; Doyle, Michael, P. Org. Lett. 2002, 4, 901.
20. Nakamura, Y.; Takeuchi, S.; Ohgo, Y.; Yamaoka, M.; Yoshida, A.; Mikami, K. Tetrahedron 1999, 55, 4959.
21. Davies, H. M. L.; Stafford, D. G.; Doan, B. D.; Houser, J. H. J. Am. Chem. Soc. 1998, 120, 3326.
22. For recent synthetic advances (a) Wender, P. A.; Haustedt, L. O.; Lim, J.; Love, J. A.; Williams, T. J.; Yoon, J.-Y. J. Am. Chem. Soc. 2006, 128, 6302.
23. (b) Sperry, J. B.; Wright, D. L. J. Am. Chem. Soc. 2005, 127, 8034. For a recent review:
24. (c) Battiste, M. A.; Pelphrey, P. M.; Wright, D. L. Chem.-Eur. J. 2006, 12, 3438.
25. Prior to recrystallization, measured enantiomeric excess of 5 matched that of 4d.
26. Doyle, M. P.; Winchester, W. R.; Hoorn, J. A. A.; Lynch, V.; Simonsen, S. H.; Ghosh, R. J. Am. Chem. Soc. 1993, 115, 9968.