Highly stereoselective and one-pot synthesis of tetra-substituted monofluoroalkenes with aldehydes and fluorobis(phenylsulfonyl)methane

Chinese Journal of Chemistry

Volumn 31, Issue 7, 2013, Pages 878-884

  Shen, Xiao ^a   Ni, Chuanfa ^a   Hu, Jinbo ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

aldehydes; fluorine; nucleophilic addition; olefination; sulfones

Indexed keywords

EID: 84880743617     PISSN: 1001604X     EISSN: 16147065     Source Type: Journal    
DOI: 10.1002/cjoc.201300365     Document Type: Article

References (39)

1. Uneyama, K., Organofluorine Chemistry, Blackwell, Oxford, 2006.
2. Kirsch, P., Modern Fluoroorganic Chemistry, Wiley-VCH, Weinheim, 2004.
3. Muller, K.; Faeh, C.; Diederich, F.,. Science, 2007, 317, 1881.
4. Jeschke, P.,. ChemBioChem, 2004, 5, 570.
5. Pagliaro, M.; Ciriminna, R.,. J. Mater. Chem., 2005, 15, 4981.
6. Wang, J.; Liu, H.,. Chin. J. Org. Chem., 2011, 31, 1785.
7. Taguchi, T.; Yanai, H., In Fluorine in Medicinal Chemistry and Chemical Biology, Ed.:, Ojima, I., Blackwell Publishing Inc, Oxford, 2009, p. 257.
8. Wong, O. A.; Shi, Y. A.,. J. Org. Chem., 2009, 74, 8377.
9. Zhou, S.; Kem, E. R.; Gullen, E.; Cheng, Y.-C.; Drach, J. C.; Tamiya, S.; Mitsuya, H.; Zemlicka, J.,. J. Med. Chem., 2006, 49, 6120.
10. For an excellent review, see, Landelle, G.; Bergeron, M.; Turcotte-Savard, M.-O.; Paquin, J.-F.,. Chem. Soc. Rev., 2011, 40, 2867.
11. Michel, D.; Schlosser, M.,. Synthesis, 1996, 1007.
12. Du, Z.; Haglund, M. J.; Pratt, L. A.; Erickson, K. L.,. J. Org. Chem., 1998, 63, 8880.
13. Purrington, S. T.; Pittman, J. H.,. Tetrahedron Lett., 1987, 28, 3901.
14. Elkik, E.,. Bull. Soc. Chim. Fr., 1967, 1569.
15. Huang, X.-H.; He, P.-Y.; Shi, G.-Q.,. J. Org. Chem., 2000, 65, 627.
16. Prakash, G. K. S.; Chacko, H.; Vaghoo, S.; Shao, N.; Gurung, L.; Mathew, T.; Olah, G. A.,. Org. Lett., 2009, 11, 1127.
17. Zhang, W.; Huang, W.; Hu, J.,. Angew. Chem., Int. Ed., 2009, 48, 9858.
18. Burton, D. J.; Cox, D. G.,. J. Am. Chem. Soc., 1983, 105, 650.
19. Tsai, H.-J.,. Tetrahedron Lett., 1996, 37, 629.
20. Lin, J.; Welch, J. T.,. Tetrahedron Lett., 1998, 39, 9613.
21. Zhu, L.; Ni, C.; Zhao, Y.; Hu, J.,. Tetrahedron, 2010, 66, 5089.
22. Aissa, C.,. Eur. J. Org. Chem., 2009, 1831.
23. Kocienski, P. J.; Bell, A.; Blakemore, P. R.,. Synlett, 2000, 365.
24. Blakemore, P. R.; Cole, W. J.; Kocienski, P. J.; Morley, A.,. Synlett, 1998, 26.
25. Baudin, J. B.; Hareau, G.; Julia, S. A.; Ruel, O.,. Tetrahedron Lett., 1991, 32, 1175.
26. Ni, C.; Li, Y.; Hu, J.,. J. Org. Chem., 2006, 71, 6829.
27. Fukuzumi, T.; Shibata, N.; Sugiura, M.; Yasui, H.; Nakamura, S.; Toru, T.,. Angew. Chem., Int. Ed., 2006, 45, 4973.
28. Ni, C.; Zhang, L.; Hu, J.,. J. Org. Chem., 2008, 73, 5699.
29. Prakash, G. K. S.; Wang, F.; Shao, N.; Mathew, T.; Rasul, G.; Haiges, R.; Stewart, T.; Olah, G. A.,. Angew. Chem., Int. Ed., 2009, 48, 5358.
30. Zhang, S.; Zhang, Y.; Ji, Y.; Li, H.; Wang, W.,. Chem. Commun., 2009, 4886.
31. Shen, X.; Zhang, L.; Zhao, Y.; Zhu, L.; Li, G.; Hu, J.,. Angew. Chem., Int. Ed., 2011, 50, 2588.
32. Shen, X.; Ni, C.; Hu, J.,. Helv. Chim. Acta, 2012, 95, 2043.
33. Zhang, W.; Ni, C.; Hu, J.,. Top. Curr. Chem., 2012, 308, 25.
34. Ni, C.; Hu, J.,. Synlett, 2011, 770.
35. Shen, X.; Zhang, W.; Ni, C.; Gu, Y.; Hu, J.,. J. Am. Chem. Soc., 2012, 134, 16999.
36. Shen, X.; Zhang, W.; Zhang, L.; Luo, T.; Wan, X.; Gu, Y.; Hu, J.,. Angew. Chem., Int. Ed., 2012, 51, 6966.
37. Furukawa, T.; Goto, Y.; Kawazoe, J.; Tokunaga, E.; Nakamura, S.; Yang, Y.; Du, H.; Kakehi, A.; Shiro, M.; Shibata, N.,. Angew. Chem., Int. Ed., 2010, 49, 1642.
38. Ni, C.; Zhang, L.; Hu, J.,. J. Org. Chem., 2009, 74, 3767.
39. CCDC 936444 (4g) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www. ccdc.cam.ac.uk/ data-request/cif.