Nucleophilic ring opening of cyclopropane hemimalonates using internal Brønsted acid activation

Organic Letters

Volumn 13, Issue 16, 2011, Pages 4180-4183

  Emmett, Michael R ^a   Kerr, Michael A ^a  

^a UNIVERSITY OF WESTERN ONTARIO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ACID; CYCLOPROPANE; CYCLOPROPANE DERIVATIVE; MALONIC ACID DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; HYDROGEN BOND;

ACIDS; CYCLOPROPANES; HYDROGEN BONDING; MALONATES; MOLECULAR STRUCTURE;

EID: 80051702325     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol201486x     Document Type: Article

References (19)

1. Bandini, M.; Eichholzer, A. Angew. Chem., Int. Ed. 2009, 48, 9608
2. Humphrey, G. R.; Kuethe, J. T. Chem. Rev. 2006, 106, 2875
3. Cacchi, S.; Fabrizi, G. Chem. Rev. 2005, 105, 2873
4. Sundberg, R. J. Indoles; Academic: New York, 1996.
5. Harrington, P. E.; Kerr, M. A. Tetrahedron Lett. 1997, 38, 5949
6. England, D. B.; Woo, T. K.; Kerr, M. A. Can. J. Chem. 2002, 80, 992
7. England, D. B.; Kuss, T. D. O.; Keddy, R. G.; Kerr, M. A. J. Org. Chem. 2001, 66, 4704
8. Kerr, M. A.; Keddy, R. G. Tetrahedron Lett. 1999, 40, 5671
9. Bajtos, B.; Yu, M.; Zhao, H.; Pagenkopf, B. L. J. Am. Chem. Soc. 2007, 129, 9631
10. Carson, C. A.; Kerr, M. A. Chem. Soc. Rev. 2009, 38, 3051
11. Rubin, M.; Rubina, M.; Gevorgyan, V. Chem. Rev. 2007, 107, 3117
12. Yu, M.; Pagenkopf, B. L. Tetrahedron 2005, 61, 321
13. Reissig, H.-U.; Zimmer, R. Chem. Rev. 2003, 103, 1151
14. Wong, H. N. C.; Hon, M. Y.; Tse, C. W.; Yip, Y. C.; Tanko, J.; Hudlicky, T. Chem. Rev. 1989, 89, 165
15. Danishefsky, S. Acc. Chem. Res. 1979, 12, 66
16. Asano, T.; le Nobel, W. J. Chem. Rev. 1978, 78, 411
17. Kotsuki, H.; Hayashida, K.; Shimanouchi, T.; Nishizawa, N. J. Org. Chem. 1996, 61, 984
18. Perreault, C.; Goudreau, S. R.; Zimmer, L. E.; Charette, A. B. Org. Lett. 2008, 10, 689
19. Klärner, F.-G.; Diedrich, M. K.; Wigger, A. E. Effect of Pressure on Organic Reactions. In Chemistry under Extreme or Non-classical Conditions; van Eldik, R.; Hubbard, C. D., Eds.; Wiley: New York, 1997; pp 109-110.