Liao Fumin , Yu Jinsheng , Zhou Jian . Recent Advances in the Highly Stereoselective Synthesis of Tri-or Tetra-substituted Monofluoroalkenes[J]. Chinese Journal of Organic Chemistry, 2017 , 37(9) : 2175 -2186 . DOI: 10.6023/cjoc201705001

[1] (a) Gelb, M. H. J. Am. Chem. Soc. 1986, 108, 3146.
(b) Damon, D. B.; Hoover, D. J. J. Am. Chem. Soc. 1990, 112, 6439.
(c) Erickson, J. A.; McLoughlin, J. I. J. Org. Chem. 1995, 60, 1626;
(d) Pesenti, C.; Viani, F. ChemBioChem 2004, 5, 590.
(e) He, Z.; Huang, Y,; Francis, V. Acta Chim. Sinica 2013, 71, 700(in Chinese) (何展荣, 黄毅勇, Francis, V., 化学学报, 2013, 71, 700.)
(f) Ni, C.; Zhu, L.; Hu, J. Acta Chim. Sinica 2015, 73, 90(in Chinese). (倪传法, 朱林桂, 胡金波, 化学学报, 2015, 73, 90.)
(g) Xiao, Y.; Pan, Q.; Zhang, X. Acta Chim. Sinica 2015, 73, 387(in Chinese). (肖玉兰, 潘强, 张新刚, 化学学报, 2015, 73, 387.)
(h) Zhang, K.; Xu, X.-H.; Qing, F.-L. Chin. J. Org. Chem. 2015, 35, 556(in Chinese). (张柯, 徐修华, 卿凤翎, 有机化学, 2015, 35, 556.)
(i) Rong, J.; Ni, C.; Wang, Y.; Kuang, C.; Gu, Y.; Hu, J. Acta Chim. Sinica 2017, 75, 105(in Chinese). (荣健, 倪传法, 王云泽, 匡翠文, 顾玉诚, 胡金波, 化学学报, 2017, 75, 105.)
[2] (a) Hiyama, T. In Organofluorine Compounds:Chemistry and Ap-plications, Ed.:Yamamoto, H., Springer-Verlag, Berlin, 2000.
(b) Fluorine in Medicinal Chemistry and Chemical Biology, Ojima, I. Ed.; Wiley-Blackwell:United Kingdom, 2009. For reaviews:
(c) Bégué, J.-P.; Bonnet-Delphon, D. J. Fluorine Chem. 2006, 127, 992.
(d) Kirk, K. L. J. Fluorine Chem. 2006, 127, 1013.
(e) Müller, K.; Faeh, C.; Diederich, F. Science 2007, 317, 1881.
(f) Hagmann, W. K. J. Med. Chem. 2008, 51, 4359.
(g) Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, V. Chem. Soc. Rev. 2008, 37, 320.
(h) Jeschke, P. ChemBioChem 2004, 5, 570.
(i) Pagliaro, M.; Ciriminna, R. J. Mater. Chem. 2005, 15, 4981.
(j) Ni, C.; Hu, J. Chem. Soc. Rev. 2016, 45, 5441.
[3] Thayer, A. M. Chem. Eng. News 2006, 84, 15.
[4] (a) Osada, S.; Sano, S.; Ueyama, M.; Chuman, Y.; Kodama, H.; Sakaguchi, K. Bioorg. Med. Chem. 2010, 18, 605.
(b) Malo-Forest, M.; Landelle, G.; Roy, J.-A.; Lacroix, J.; Gaudreault, R.-C.; Paquin, J.-F. Bioorg. Med. Chem. Lett. 2013, 23, 1712.
(c) Dutheuil, G.; Couve-Bonnaire, S.; Pannecoucke, X. Angew. Chem. Int. Ed. 2007, 46, 1290.
(d) Wong, O. A.; Shi, Y. A. J. Org. Chem. 2009, 74, 8377.
(e) Guérin, D.; Gaumont, A.-C.; Dez, I.; Mauduit, M.; Couve-Bonnaire, S.; Pannecoucke, X. ACS Catal. 2014, 4, 2374.
(f) Dai, W.; Xiao, J.; Jin, G.; Wu, J.; Cao, S. J. Org. Chem. 2014, 79, 10537.
[5] (a) Shen, Q.; Huang, Y.-G.; Liu, C.; Xiao, J.-C.; Chen, Q.-Y.; Guo, Y. J. Fluorine Chem. 2015, 179, 14.
(b) Tian, P.; Feng, C.; Loh, T.-P. Nat. Commun. 2015, 6, 7472.
(c) Zhang, X.; Lin, Y.; Zhang, J.; Cao, S. RSC Adv. 2015, 5, 7905.
(d) Wu, J.; Xiao, J.; Dai, W.; Cao, S. RSC Adv. 2015, 5, 34498.
(e) Xiong, Y.; Huang, T.; Ji, X.; Wu, J.; Cao, S. Org. Biomol. Chem. 2015, 13, 7398.
(f) Dai, W.; Shi, H.; Zhao, X.; Cao, S. Org. Lett. 2016, 18, 4284.
(g) Kong, L.; Zhou, X.; Li, X. Org. Lett. 2016, 18, 6320.
[6] (a) Liu, G. Org. Biomol. Chem. 2012, 10, 6243.
(b) Akana, J. A.; Bhattacharyya, K. X.; Müller, P.; Sadighi, J. P. J. Am. Chem. Soc. 2007, 129, 7736.
(c) Gorske, B. C.; Mbofana, C. T.; Miller, S. J. Org. Lett. 2009, 11, 4318.
(d) Schuler, M.; Silva, F.; Bobbio, C.; Tessier, A.; Gouverneur, V. Angew. Chem. Int. Ed. 2008, 47, 7927.
(e) de Haro, T.; Nevado, C. Chem. Commun. 2011, 47, 248;
(f) Lan, Y.; Hammond, G. B. Org. Lett. 2002, 4, 2437.
(g) Zhou, C.; Ma, Z.; Gu, Z.; Fu, C.; Ma, S. J. Org. Chem. 2008, 73, 772.
(h) Cui, H. F.; Chai, Z.; Zhao, G.; Zhu, S. Z. Chin. J. Chem. 2009, 27, 189.
(i) Lü, B.; Fu, C.; Ma, S. Org. Biomol. Chem. 2010, 8, 274.
[7] (a) Couve-Bonnaire, S.; Cahard, D.; Pannecoucke, X. Org. Biomol. Chem. 2007, 5, 1151.
(b) Yanai, H.; Taguchi, T. Eur. J. Org. Chem. 2011, 5939.
(c) Landelle, G.; Bergeron, M.; Turcotte-Savard, M.-O.; Paquin, J.-F. Chem. Soc. Rev. 2011, 40, 2867.
(d) Champagne, P. A.; Desroches, J.; Hamel, J.-D.; Vandamme, M.; Paquin, J.-F. Chem. Rev. 2015, 115, 9073.
(e) Drouin, M.; Hamel, J.-D.; Paquin, J.-F. Synlett 2016, 27, 821.
(f) Zhang, X.; Cao, S. Tetrahedron Lett. 2017, 58, 375.
[8] Schlosser, M.; Zimmermann, M. Synthesis 1969, 75.
[9] Cox, D. G.; Gurusamy, N.; Burton, D. J. J. Am. Chem. Soc. 1985, 107, 2811.
[10] (a) Lei, X. S.; Dutheuil, G.; Pannecoucke, X.; Quirion, J. C. Org. Lett. 2004, 6, 2101.
(b) Zoute, L.; Dutheuil, G.; Quirion, J.-C.; Jubault, P.; Pannecoucke, X. Synthesis 2006, 3409.
[11] Burton, D. J.; Yang, Z.-Y.; Qiu, W. Chem. Rev. 1996, 96, 1641.
[12] Machleidt, H.; Wessendorf, R. Justus Liebigs Ann. Chem. 1964, 674, 1.
[13] Moghadam, G. E.; Penne, J. S. Bull. Soc. Chim. Fr. 1985, 448.
[14] Sano, S.; Matsumoto, T.; Nakao, M. Tetrahedron Lett. 2014, 55, 4480.
[15] Chevrie, D.; Lequeux, T.; Demoute, J. P.; Pazenok, S. Tetrahedron Lett. 2003, 44, 8127.
[16] Ghosh, A. K.; Zajc, B. Org. Lett. 2006, 8, 1553.
[17] (a) Zajc, B.; Kake, S. Org. Lett. 2006, 8, 4457.
(b) Pfund, E.; Lebargy, C.; Rouden, J.; Lequeux, T. J. Org. Chem. 2007, 72, 7871.
[18] (a) Ghosh, A. K.; Banerjee, S.; Sinha, S.; Kang, S. B.; Zajc, B. J. Org. Chem. 2009, 74, 3689.
(b) He, M.; Ghosh, A. K.; Zajc, B. Synlett 2008, 999.
[19] Alonso, D. A.; Fuensanta, M.; Gómez-Bengoa, E.; Nájera, C. Adv. Synth. Catal. 2008, 350, 1823.
[20] Larnaud, F.; Pfund, E.; Linclau, B.; Lequeux, T. Tetrahedron 2014, 70, 5632.
[21] Zhao, Y.; Jiang, F.; Hu, J. J. Am. Chem. Soc. 2015, 137, 5199.
[22] Satoh, T.; Itoh, N.; Onda, K.; Kitoh, Y.; Yamakawa, K. Bull. Chem. Soc. Jpn. 1992, 65, 2800.
[23] Chevrie, D.; Lequeux, T.; Pommelet, J.-C. Org. Lett. 1999, 1, 1539.
[24] Boys, M. L.; Collington, E. W.; Finch, H.; Swanson, S.; Whitehead, J. F. Tetrahedron Lett. 1988, 29, 3365.
[25] (a) Zhang, W.; Huang, W.; Hu, J. Angew. Chem. Int. Ed. 2009, 48, 9858.
(b) Shen, X.; Hu, J. Eur. J. Org. Chem. 2014, 4437.
(c) Liu, Q.; Shen, X.; Ni, C.; Hu, J. Angew. Chem. Int. Ed. 2017, 56, 619.
[26] Welch, J. T.; Herbert, R. W. J. Org. Chem. 1990, 55, 4782.
[27] [Michida, M.; Mukaiyama, T. Chem. Lett. 2008, 37, 890.
[28] (a) Barma, D. K.; Kundeu, A.; Zhang, H.; Mioskowski, C.; Falck, J. R. J. Am. Chem. Soc. 2003, 125, 3218.
(b) Falck, J. R.; Bojet, R.; Barma, D. K.; Bandyopadhyay, A.; Joseph, S.; Mioskowski, C. J. Org. Chem. 2006, 71, 8178.
(c) Feng, Z.; Min, Q.-Q.; Zhao, H.-Y.; Gu, J.-W.; Zhang, X.Angew. Chem. Int. Ed. 2015, 54, 1270.
[29] Lemonnier, G.; Zoute, L.; Dupas, G.; Quirion, J.-C.; Jubault, P. J. Org. Chem. 2009, 74, 4124.
[30] Augustine, J.-K.; Bombrun, A.; Venkatachaliah, S.; Jothi, A. Org. Biomol. Chem. 2013, 11, 8065.
[31] Cao, C.-R.; Ou, S.; Jiang, M.; Liu, J.-T. Org. Biomol. Chem. 2014, 12, 467.
[32] (a) Grundmann, C. Justus. Liebigs Ann. Chem. 1938, 536, 29.
(b) Font, J.; Serratosa, F.; Valls, J. Chem. Commun. 1970, 721.
(c) Kulkowit, S.; McKervey, M. A. J. Chem. Soc., Chem. Commun. 1978, 1069.
(d) Baratta, W.; Del Zotto, A.; Rigo, P. Chem. Commun. 1997, 2163.
(e) Del Zotto, A.; Baratta, W.; Verardo, G.; Rigo, P. Eur. J. Org. Chem. 2000, 2795.
(f) Doyle, M. P.; Hu, W.; Phillips, I. M. Org. Lett. 2000, 2, 1777.
(g) Greenman, K. L.; Carter, D. S.; Van Vranken, D. L. Tetrahedron 2001, 57, 5219.
(h) Doyle, M. P.; Yan, M. J. Org. Chem. 2002, 67, 602;
(i) Li, G.-Y.; Che, C.-M. Org. Lett. 2004, 6, 1621.
(j) Hodgson, D. M.; Angrish, D. Chem. Commun. 2005, 4902.
(k) Chen, S.; Wang, J. Chem. Commun. 2008, 4198;
(l) Xiao, Q.; Ma, J.; Yang, Y.; Zhang, Y.; Wang, J. Org. Lett. 2009, 11, 4732.
(m) Hansen, J. H.; Parr, B. T.; Pelphrey, P.; Jin, Q.; Autschbach, J.; Davies, H. M. L.Angew. Chem. Int. Ed. 2011, 50, 2544.
(n) Xia, Y.; Liu, Z.; Xiao, Q.; Qu, P.; Ge, R.; Zhang, Y.; Wang, J. Angew. Chem. Int. Ed. 2012, 51, 5714.
(o) Hu, M.; He, Z.; Gao, B.; Li, L.; Ni, C.; Hu, J. J. Am. Chem. Soc. 2013, 135, 17302.
(p) Xiao, Q.; Zhang, Y.; Wang, J. Acc. Chem. Res. 2013, 46, 236.
(q) Zhang, D.; Xu, G.; Ding, D.; Zhu, C.; Li, J.; Sun, J. Angew. Chem. Int. Ed. 2014, 53, 11070.
(r) Hu, M.; Ni, C.; Li, L.; Han, Y.; Hu, J. J. Am. Chem. Soc. 2015, 137, 14496.
(s) Zhu, C.; Xu, G.; Liu, K.; Qiu, L.; Peng, S.; Sun, J. Chem. Commun. 2015, 51, 12768.
(t) Zhu, C.; Xu, G.; Ding, D.; Qiu, L.; Sun, J. Org. Lett. 2015, 17, 4244.
(u) Zhang, Z.; Yu, W.; Wu, C.; Wang, C.; Zhang, Y.; Wang, J. Angew. Chem. Int. Ed. 2016, 55, 273.
(v) Feng, S.; Mo, F.; Xia, Y.; Liu, Z.; Liu, Z.; Zhang, Y.; Wang, J. Angew. Chem. Int. Ed. 2016, 55, 15401.
[33] (a) Fuchigami, T.; Hayashi, T.; Konno, A. Tetrahedron Lett. 1992, 33, 3161.
(b) Usuki, Y.; Iwaoka, M.; Tomoda, S. J. Chem. Soc., Chem. Commun. 1992, 1148.
[34] (a) Ivanova, M. V.; Bayle, A.; Besset, T.; Pannecoucke, X.; Poisson, T. Angew. Chem. Int. Ed. 2016, 55, 14141.
(b) Feng, Z.; Min, Q.-Q.; Xiao, Y.-L.; Zhang, B.; Zhang, X.Angew. Chem. Int. Ed. 2014, 53, 1669.
[35] (a) Cao, Z.-Y.; Wang, X.; Tan, C.; Zhao, X.-L.; Zhou, J.; Ding, K. J. Am. Chem. Soc. 2013, 135, 8197.
(b) Cao, Z.-Y.; Zhao, Y.-L.; Zhou, J. Chem. Commun. 2016, 52, 2537.
(c) Zhao, Y.-L.; Cao, Z.-Y.; Zeng, X.-P.; Shi, J.-M.; Yu, Y.-H.; Zhou, J. Chem. Commun. 2016, 52, 3943.
[36] For a review, see:
(a) Decostanzi, M.; Campagne, J.-M.; Leclerc, E. Org. Biomol. Chem. 2015, 13, 7351. For examples, see:
(b) Amii, H.; Kobayashi, T.; Hatamoto, Y.; Uneyama, K. Chem. Commun. 1999, 1323.
(c) Chu, L.; Zhang, X.; Qing, F.-L. Org. Lett. 2009, 11, 2197.
(d) Yuan, Z.; Wei, Y.; Shi, M. Chin. J. Chem. 2010, 28, 1709.
(e) Kashikura, W.; Mori, K.; Akiyama, T. Org. Lett. 2011, 13, 1860. For our continuous efforts in the functionalization of fluorinated enol silyl ethers, see:
(f) Liu, Y.-L.; Zhou, J. Chem. Commun. 2012, 48, 1919.
(g) Liu, Y.-L.; Zeng, X.-P.; Zhou, J. Acta Chim. Sinica. 2012, 70, 1451.
(h) Liu, Y.-L.; Liao, F.-M.; Niu, Y.-F.; Zhao, X.-L.; Zhou, J. Org. Chem. Front. 2014, 1, 742.
(i) Yu, J.-S.; Liu, Y.-L.; Tang, J.; Wang, X.; Zhou, J. Angew. Chem. Int. Ed. 2014, 53, 9512.
(j) Liao, F.-M.; Liu, Y.-L.; Yu, J.-S.; Zhou, F.; Zhou, J. Org. Biomol. Chem. 2015, 13, 8906.
(k) Yu, J.-S.; Zhou, J. Org. Biomol. Chem. 2015, 13, 10968.
(l) Yu, J.-S.; Liao, F.-M.; Gao, W.-M.; Liao, K.; Zuo, R.-L.; Zhou, J. Angew. Chem. Int. Ed. 2015, 54, 7381.
(m) Yu, J.-S.; Zhou, J. Org. Chem. Front. 2016, 3, 298.
(n) Zeng, X.-P.; Zhou, J. J. Am. Chem. Soc. 2016, 138, 8730.
[37] Liao, F.-M.; Cao, Z.-Y.; Yu, J.-S.; Zhou, J. Angew. Chem. Int. Ed. 2017, 56, 2459.
[38] (a) Okoromoba, O. E.; Han, J.; Hammond, G. B.; Xu, B. J. Am. Chem. Soc. 2014, 136, 14381.
(b) Nahra, F.; Patrick, S. R.; Bello, D.; Brill, M.; Obled, A.; Cordes, D. B.; Slawin, A. M. Z.; O'Hagan, D.; Nolan, S. P. ChemCatChem 2015, 7, 240.
(c) Li, Y.; Liu, X.; Ma, D.; Liu, B.; Jiang, H. Adv. Synth. Catal. 2012, 354, 2683.
[39] (a) Lee, S. H.; Schwartz, J. J. Am. Chem. Soc. 1986, 108, 2445.
(b) Tius, M. A.; Kawakami, J. K. Tetrahedron 1995, 51, 3997.
(c) Sommer, H.; Fürstner A. Chem. Eur. J. 2017, 23, 558.
(d) Petasis, N. A.; Yudin, A. K.; Zavialov, I. A.; Prakash, G. K. S.; Olah, G. A. Synlett 1997, 606.
(e) Furuya, T.; Ritter, T. Org. Lett. 2009, 11, 2860.
(f) Tredwell, M.; Gourverneur, V. Org. Biomol. Chem. 2006, 4, 26.
(g) Yang, M.-H.; Matikonda, S. S.; Altman, R. A. Org. Lett. 2013, 15, 3894.
(h) Ye, Y.; Takada, T.; Buchwald, S. L. Angew. Chem. Int. Ed. 2016, 55, 15559.
[40] (a) Qiu, S.; Xu, T.; Zhou, J.; Guo, Y.; Liu, G. J. Am. Chem. Soc. 2010, 132, 2856;
(b) Shao, Q.; Huang, Y. Chem. Commun. 2015, 51, 6584.