A straightforward and highly diastereoselective access to functionalized monofluorinated cyclopropanes via a michael initiated ring closure reaction

Organic Letters

Volumn 15, Issue 21, 2013, Pages 5598-5601

  Ferrary, Thibault ^a   David, Emilie ^a   Milanole, Gaëlle ^a   Besset, Tatiana ^a   Jubault, Philippe ^a   Pannecoucke, Xavier ^a  

^a UNIVERSITÉ DE ROUEN   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; AMMONIUM DERIVATIVE; CYCLOPROPANE DERIVATIVE; FLUORINATED HYDROCARBON;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ALKENES; AMMONIUM COMPOUNDS; CATALYSIS; CYCLOPROPANES; HYDROCARBONS, FLUORINATED; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 84887104751     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol402837u     Document Type: Article

References (29)

1. Chen, D.Y.-K.; Pouwer, R. H.; Richard, J.-A. Chem. Soc. Rev. 2012, 41, 4631
2. Pellissier, H. Tetrahedron 2008, 64, 7041
3. Pietruszka, J. Chem. Rev. 2003, 103, 1051
4. Donaldson, W. A. Tetrahedron 2001, 57, 8589
5. Faust, D. Angew. Chem., Int. Ed. 2001, 40, 2251
6. Salaun, J. Top. Curr. Chem. 2000, 207, 1
7. Liang, T.; Neumann, C. N.; Ritter, T. Angew. Chem., Int. Ed. 2013, 52, 8214
8. Ma, J. A.; Cahard, D. Chem. Rev. 2004, 104, 6119
9. Ma, J.-A.; Cahard, D. Chem. Rev. 2008, 108, PR1
10. Pessah, N.; Bialer, M.; Wlodarczyk, B.; Finnell, R. H.; Yagen, B. J. Med. Chem. 2009, 52, 2233
11. Chaki, S.; Yoshikawa, R.; Hirota, S.; Shimazaki, T.; Maeda, M.; Kawashima, N.; Yoshimizu, T.; Yasuhara, A.; Sakagami, K.; Okuyama, S.; Nakanishi, S.; Nakazato, A. Neuropharmacology 2004, 46, 457
12. Lemonnier, G.; Lion, C.; Quirion, J.-C.; Pin, J.-P.; Goudet, C.; Jubault, P. Bioorg. Med. Chem. 2012, 20, 4716
13. Wang, H.; Guptill, D. M.; Varela Alvarez, A.; Musaev, D. G.; Davies, H. M. L. Chem. Sci. 2013, 4, 2844
14. Beaulieu, L.-P. B.; Schneider, J. F.; Charette, A. B. J. Am. Chem. Soc. 2013, 135, 7819
15. Oshiro, K.; Morimoto, Y.; Amii, H. Synthesis 2010, 2080
16. Fedoryński, M. Chem. Rev. 2003, 103, 1099
17. Grygorenko, O. O.; Artamonov, O. S.; Komarov, I. V.; Mykhailiuk, P. K. Tetrahedron 2011, 67, 803
18. Morandi, B.; Carreira, E. M. Angew. Chem., Int. Ed. 2010, 49, 938
19. Hirotaki, K.; Takehiro, Y.; Kamaishi, R.; Yamada, Y.; Hanamoto, T. Chem. Commun. 2013, 49, 7965
20. Zheng, J.; Lin, J.-H.; Cai, J.; Xiao, J.-C. Chem.-Eur. J. 2013, 10.1002/chem.201303248
21. David, E.; Milanole, G.; Ivashkin, P.; Couve-Bonnaire, S.; Jubault, P.; Pannecoucke, X. Chem.-Eur. J. 2012, 18, 14904 and references therein
22. Saito, A.; Ito, H.; Taguchi, T. Tetrahedron 2001, 57, 7487
23. Sun, X.-L.; Tang, Y. Acc. Chem. Res. 2008, 41, 937 and references therein
24. Papageorgiou, C. D.; Ley, S. V.; Gaunt, M. J. Angew. Chem., Int. Ed. 2003, 42, 828
25. Papageorgiou, C. D.; Cubillo de Dios, M. A.; Ley, S. V.; Gaunt, M. J. Angew. Chem., Int. Ed. 2004, 116, 4741
26. Shen, X.; Zhang, W.; Zhang, L.; Luo, T.; Wan, X.; Gu, Y.; Hu, J. Angew. Chem., Int. Ed. 2012, 51, 6966
27. Ivashkin, P.; Couve-Bonnaire, S.; Jubault, P.; Pannecoucke, X. Org. Lett. 2012, 14, 5130
28. Ivashkin, P.; Couve-Bonnaire, S.; Jubault, P.; Pannecoucke, X. Org. Lett. 2012, 14, 2270
29. Milanole, G.; Couve-Bonnaire, S.; Bonfanti, J.-F.; Jubault, P.; Pannecoucke, X. J. Org. Chem. 2013, 78, 212