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http://dx.doi.org/10.5012/bkcs.2014.35.6.1851

Studies on the C/O-regioselectivity in Electrophilic Fluoromethylations of β-Ketoesters based on Thermodynamics by Ab initio Calculations  

Yang, Yu-Dong (Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology)
Wang, Xin (Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology)
Tsuzuki, Seiji (Research Initiative of Computational Sciences (RICS), Nanosystem Research Institute (NRI), National Institute of Advanced Industrial Science and Technology (AIST))
Tokunaga, Etsuko (Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology)
Shibata, Norio (Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology)
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Keywords
C-alkylation; Enolates; Fluoromethylation; O-alkylation; Regioselectivity;
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1 Head-Gordon, M.; Pople, J. A.; Frisch, M. J. Chem. Phys. Lett. 1988, 153, 503.   DOI   ScienceOn
2 Hu, J.; Zhang, W.; Wang, F. Chem. Commun. 2009, 7465.
3 Moller, C.; Plesset, M. S. Phys. Rev. 1934, 46, 618.   DOI
4 Ransil, B. J. J. Chem. Phys. 1961, 34, 2109.   DOI
5 Boys, S. F.; Bernardi, F. Mol. Phys. 1970, 19, 553.   DOI   ScienceOn
6 Singh, U. C.; Kollman, P. A. J. Comput. Chem. 1984, 5, 129.   DOI
7 Besler, B. H.; Mertz, K. M.; Kollman, P. A. J. Comput. Chem. 1990, 11, 431.   DOI
8 (a) Shen, X.; Zhou, M.; Ni, C.; Zhang, W.; Hu, J. Chem. Sci. 2014, 5, 117.   DOI
9 (b) Shen, X.; Zhang, W.; Ni, C.; Gu, Y.; Hu, J. J. Am. Chem. Soc. 2012, 134, 16999.   DOI
10 (c) Shen, X.; Zhang, W.; Zhang, L.; Luo, T.; Wan, X.; Gu, Y.; Hu, J. Angew. Chem. Int. Ed. 2012, 51, 6966.   DOI
11 (d) Kowalczyk, R.; Edmunds, A. J. F.; Hall, R. G.; Bolm, C. Org. Lett. 2011, 13, 768.   DOI
12 (e) Urban, C.; Cadoret, F.; Blazejewski, J.-C.; Magnier, E. Eur. J. Org. Chem. 2011, 4862.
13 (f) Nomura, Y.; Tokunaga, E.; Shibata, N. Angew. Chem. Int. Ed. 2011, 50, 1885.   DOI
14 (g) Prakash, G. K. S.; Zhang, Z.; Wang, F.; Ni, C.; Olah, G. A. J. Fluorine. Chem. 2011, 132, 792.   DOI
15 (h) Zhang, W.; Wang, F.; Hu, J. Org. Lett. 2009, 11, 2019.   DOI
16 (i) Zhang, W.; Hu, J. Adv. Synth. Catal. 2010, 352, 2799.   DOI
17 (j) Noritake, S.; Shibata, N.; Nakamura, S.; Toru, T.; Shiro, M. Eur. J. Org. Chem. 2008, 3465.
18 Yang, Y.-D.; Lu, X.; Liu, G.; Tokunaga, E.; Tsuzuki, S.; Shibata, N. ChemistryOpen 2012, 1, 221.   DOI
19 Macr, Y.; Pradet, C.; Popkin, M.; Blazejewski, J.-C.; Magnier, E. Tetrahedron Lett. 2010, 51, 5388.   DOI
20 (a) Macr, Y.; Magnier, E. Eur. J. Org. Chem. 2012, 2479.
21 (b) Shibata, N.; Matsnev, A.; Cahard, D. Beilstein J. Org. Chem. 2010, 6, No. 65.
22 House, H. O. Modern Synthetic Reactions, 2nd ed.; Benjamin, W. A., Ed.; Menlo Park: CA, 1972.
23 Rhoads, S. J.; Hasbrouck, R. W. Tetrahedron 1966, 22, 3557.   DOI
24 Reutov, O. A.; Beletskaya, I. P.; Kurts, A. L. Ambident Anions; Michael, J. P., Ed.; Plenum: New York, USA, 1983.
25 Eames, J. In Chemistry of Metal Enolates; Zabicky, J., Ed.; John Wiley & Sons: West Sussex, England, 2009; Ch. 8, pp 411-460.
26 Kurz, A. L.; Baletskaya, I. P.; Macias, A.; Reutov, O. A. Tetrahedron Lett. 1968, 9, 3679.   DOI
27 Pickersgill, I. F.; Marchington, A. P.; Rayner, C. M. J. Chem. Soc. Chem. Commun. 1994, 2597.
28 (a) Kobayashi, M.; Umemura, K.; Watanabe, N.; Matsuyama, H. Chem. Lett. 1985, 14, 1067.
29 (b) Kobayashi, M.; Umemura, K.; Matsuyama, H. Chem. Lett. 1987, 16, 327.
30 Umemura, K.; Matsuyama, H.; Watanabe, N.; Kobayashi, M.; Kamigata, N. J. Org. Chem. 1989, 54, 2374.   DOI
31 Kirsch, P. Modern Fluoroorganic Chemistry: Synthesis, Reactivity, Applications; Wiley-VCH: Weinheim, Germany, 2004.
32 Liu, G.; Wang, X.; Xu, X.-H.; Lu, X.; Tokunaga, E.; Tsuzuki, S.; Shibata, N. Org. Lett. 2013, 15, 1044.   DOI
33 Prakash, G. K. S.; Jog, P. V.; Batamack, P. T. D.; Olah, G. A. Science 2012, 338, 1324.   DOI
34 Damoun, S.; Van de Woude, G.; Choho, K.; Geerlings, P. J. Phys. Chem. A 1999, 103, 7861.   DOI
35 Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A.; Peralta, J. E., Jr.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, J. M.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, O.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian 09, Revision C. 01; Gaussian, Inc.: Wallingford, CT, 2009.