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Kinetic Resolution of Allyl Fluorides by Enantioselective Allylic Trifluoromethylation Based on Silicon‐Assisted CF Bond Cleavage

2013; Wiley; Volume: 53; Issue: 2 Linguagem: Inglês

10.1002/anie.201308071

ISSN

1521-3773

Autores

Takayuki Nishimine, Kazunobu Fukushi, Naoyuki Shibata, Hiromi Taira, Etsuko Tokunaga, Akihito Yamano, Motoo Shiro, Norio Shibata,

Tópico(s)

Carbohydrate Chemistry and Synthesis

Resumo

Angewandte Chemie International EditionVolume 53, Issue 2 p. 517-520 Communication Kinetic Resolution of Allyl Fluorides by Enantioselective Allylic Trifluoromethylation Based on Silicon-Assisted CF Bond Cleavage† Takayuki Nishimine, Takayuki Nishimine Department of Frontier Materials, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya, 466-8555 (Japan)Search for more papers by this authorKazunobu Fukushi, Kazunobu Fukushi Department of Frontier Materials, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya, 466-8555 (Japan)Search for more papers by this authorNaoyuki Shibata, Naoyuki Shibata Department of Frontier Materials, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya, 466-8555 (Japan)Search for more papers by this authorHiromi Taira, Hiromi Taira Department of Frontier Materials, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya, 466-8555 (Japan)Search for more papers by this authorEtsuko Tokunaga, Etsuko Tokunaga Department of Frontier Materials, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya, 466-8555 (Japan)Search for more papers by this authorAkihito Yamano, Akihito Yamano Rigaku Corporation, 3-9-12 Matsubara-cho, Akishima, Tokyo, 196-8666 (Japan)Search for more papers by this authorDr. Motoo Shiro, Dr. Motoo Shiro Rigaku Corporation, 3-9-12 Matsubara-cho, Akishima, Tokyo, 196-8666 (Japan)Search for more papers by this authorProf. Dr. Norio Shibata, Corresponding Author Prof. Dr. Norio Shibata [email protected] Department of Frontier Materials, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya, 466-8555 (Japan)Department of Frontier Materials, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya, 466-8555 (Japan)Search for more papers by this author Takayuki Nishimine, Takayuki Nishimine Department of Frontier Materials, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya, 466-8555 (Japan)Search for more papers by this authorKazunobu Fukushi, Kazunobu Fukushi Department of Frontier Materials, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya, 466-8555 (Japan)Search for more papers by this authorNaoyuki Shibata, Naoyuki Shibata Department of Frontier Materials, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya, 466-8555 (Japan)Search for more papers by this authorHiromi Taira, Hiromi Taira Department of Frontier Materials, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya, 466-8555 (Japan)Search for more papers by this authorEtsuko Tokunaga, Etsuko Tokunaga Department of Frontier Materials, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya, 466-8555 (Japan)Search for more papers by this authorAkihito Yamano, Akihito Yamano Rigaku Corporation, 3-9-12 Matsubara-cho, Akishima, Tokyo, 196-8666 (Japan)Search for more papers by this authorDr. Motoo Shiro, Dr. Motoo Shiro Rigaku Corporation, 3-9-12 Matsubara-cho, Akishima, Tokyo, 196-8666 (Japan)Search for more papers by this authorProf. Dr. Norio Shibata, Corresponding Author Prof. Dr. Norio Shibata [email protected] Department of Frontier Materials, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya, 466-8555 (Japan)Department of Frontier Materials, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya, 466-8555 (Japan)Search for more papers by this author First published: 07 November 2013 https://doi.org/10.1002/anie.201308071Citations: 85 † This study was financially supported in part by Kakenhi (25288045, 24105513, Project No. 2304: Advanced Molecular Transformation by Organocatalysts) and JST (ACT-C). Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onEmailFacebookTwitterLinkedInRedditWechat Graphical Abstract Two birds, one stone! The first kinetic resolution of allyl fluorides was achieved by the development of an organocatalyzed enantioselective allylic trifluoromethylation. Two kinds of chiral fluorinated compounds, which incorporate C*F and C*CF3 units, respectively, can thus be accessed by a single transformation. Supporting Information As a service to our authors and readers, this journal provides supporting information supplied by the authors. Such materials are peer reviewed and may be re-organized for online delivery, but are not copy-edited or typeset. Technical support issues arising from supporting information (other than missing files) should be addressed to the authors. Filename Description anie_201308071_sm_miscellaneous_information.pdf5.1 MB miscellaneous_information Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article. References 1 1aK. L. Kirk, J. Fluorine Chem. 2006, 127, 1013–1029; 1bK. L. Kirk, Org. Process Res. Dev. 2008, 12, 305–321; 1cI. Ojima, Fluorine in Medicinal Chemistry and Chemical Biology, Wiley-Blackwell, Oxford, 2009. 2 2aM. Hird, Chem. Soc. Rev. 2007, 36, 2070–2095; 2bZ. Hong, S. G. Weber, Teflon AF Materials in Topics in Current Chemistry, Vol. 308 (Ed.: ), Springer, Berlin, 2012, pp. 307–377. 3 3aK. Uneyama, Organofluorine Chemistry, Blackwell, Oxford, 2006; 3bJ.-A. Ma, D. Cahard, Chem. Rev. 2008, 108, PR 1–PR43; 3cN. Shibata, S. Mizuta, H. Kawai, Tetrahedron: Asymmetry 2008, 19, 2633–2644; 3dJ. Nie, H.-C. Guo, D. Cahard, J.-A. Ma, Chem. Rev. 2011, 111, 455–529; 3eC. Hollingworth, V. Gouverneur, Chem. Commun. 2012, 48, 2929–2942; 3fT. Liang, C. N. Neumann, T. Ritter, Angew. Chem. 2013, 125, 8372–8423; Angew. Chem. Int. Ed. 2013, 52, 8214–8264. 4 4aE. Vedejs, M. Jure, Angew. Chem. 2005, 117, 4040–4069; Angew. Chem. Int. Ed. 2005, 44, 3974–4001; 4bH. Pellissier, Adv. Synth. Catal. 2011, 353, 1613–1666. 5 5aH. Amii, K. Uneyama, Chem. Rev. 2009, 109, 2119–2183; 5bT. Stahl, H. F. T. Klare, M. Oestreich, ACS Catal. 2013, 3, 1578–1587. 6For examples of the activation of allylic CF bonds, see: 6aK. Hirano, H. Yorimitsu, K. Oshima, Org. Lett. 2004, 6, 4873–4875; 6bK. Hirano, K. Fujita, H. Yorimitsu, H. Shinokubo, K. Oshima, Tetrahedron Lett. 2004, 45, 2555–2557; 6cL. Hintermann, F. Läng, P. Maire, A. Togni, Eur. J. Inorg. Chem. 2006, 1397–1412; 6dM. Bergeron, T. Johnson, J.-F. Paquin, Angew. Chem. 2011, 123, 11308–11312; Angew. Chem. Int. Ed. 2011, 50, 11112–11116; 6eD. Watanabe, M. Koura, A. Saito, H. Yanai, Y. Nakamura, M. Okada, A. Sato, T. Taguchi, J. Fluorine Chem. 2011, 132, 327–338; 6fM. Bergeron, D. Guyader, J.-F. Paquin, Org. Lett. 2012, 14, 5888–5891. 7 7aA. Hazari, V. Gouverneur, J. M. Brown, Angew. Chem. 2009, 121, 1322–1325; Angew. Chem. Int. Ed. 2009, 48, 1296–1299; 7bE. Benedetto, M. Keita, M. Tredwell, C. Hollingworth, J. M. Brown, V. Gouverneur, Organometallics 2012, 31, 1408–1416. 8 8aX. Pigeon, M. Bergeron, F. Barabé, P. Dubé, H. N. Frost, J.-F. Paquin, Angew. Chem. 2010, 122, 1141–1145; Angew. Chem. Int. Ed. 2010, 49, 1123–1127; 8bJ.-F. Paquin, Synlett 2011, 289–293. 9G. Haufe, S. Suzuki, H. Yasui, C. Terada, T. Kitayama, M. Shiro, N. Shibata, Angew. Chem. 2012, 124, 12441–12445; Angew. Chem. Int. Ed. 2012, 51, 12275–12279. 10Alkyl-substituted compounds with less bulky groups, such as methyl substituents, are poor substrates for this transformation; see: T. Furukawa, T. Nishimine, E. Tokunaga, K. Hasegawa, M. Shiro, N. Shibata, Org. Lett. 2011, 13, 3972–3975; see also Ref. [14]. 11For the construction of chiral C*CF3 centers, see: 11aS. Mizuta, N. Shibata, S. Akiti, H. Fujimoto, S. Nakamura, T. Toru, Org. Lett. 2007, 9, 3707–3710; 11bS. Noritake, N. Shibata, Y. Nomura, Y. Huang, A. Matsnev, S. Nakamura, T. Torua, D. Cahard, Org. Biomol. Chem. 2009, 7, 3599–3604; 11cH. Kawai, A. Kusuda, S. Nakamura, M. Shiro, N. Shibata, Angew. Chem. 2009, 121, 6442–6445; Angew. Chem. Int. Ed. 2009, 48, 6324–6327; 11dH. Kawai, K. Tachi, E. Tokunaga, M. Shiro, N. Shibata, Org. Lett. 2010, 12, 5104–5107; see also Ref. [3]. 12For the construction of chiral C*F centers, see: 12aN. Shibata, E. Suzuki, Y. Takeuchi, J. Am. Chem. Soc. 2000, 122, 10728–10729; 12bN. Shibata, E. Suzuki, T. Asahi, M. Shiro, J. Am. Chem. Soc. 2001, 123, 7001–7009; 12cN. Shibata, J. Kohno, K. Takai, T. Ishimaru, S. Nakamura, T. Toru, S. Kanemasa, Angew. Chem. 2005, 117, 4276–4279; Angew. Chem. Int. Ed. 2005, 44, 4204–4207; 12dD. S. Reddy, N. Shibata, J. Nagai, S. Nakamura, T. Toru, S. Kanemasa, Angew. Chem. 2008, 120, 170–174; Angew. Chem. Int. Ed. 2008, 47, 164–168. 13 13aD. Basavaiah, B. S. Reddy, S. S. Badsara, Chem. Rev. 2010, 110, 5447–5674; 13bT.-Y. Liu, M. Xie, Y.-C. Chen, Chem. Soc. Rev. 2012, 41, 4101–4112; 13cR. Rios, Catal. Sci. Technol. 2012, 2, 267–278. 14T. Furukawa, J. Kawazoe, W. Zhang, T. Nishimine, E. Tokunaga, T. Matsumoto, M. Shiro, N. Shibata, Angew. Chem. 2011, 123, 9858–9862; Angew. Chem. Int. Ed. 2011, 50, 9684–9688. 15X. Companyó, G. Valero, V. Ceban, T. Calvet, M. Font-Bardía, A. Moyano, R. Rios, Org. Biomol. Chem. 2011, 9, 7986–7989. 16 16aJ. N. Kim, H. J. Lee, J. H. Gong, Tetrahedron Lett. 2002, 43, 9141–9146; 16bM. G. Nascimento, S. P. Zanotto, S. P. Melegari, L. Fernandes, M. M. Sá, Tetrahedron: Asymmetry 2003, 14, 3111–3115; 16cC.-W. Cho, J.-R. Kong, M. J. Krische, Org. Lett. 2004, 6, 1337–1339; 16dC. E. Aroyan, M. M. Vasbinder, S. J. Miller, Org. Lett. 2005, 7, 3849–3851; 16eC. Ó. Dálaigh, S. J. Connon, J. Org. Chem. 2007, 72, 7066–7069; 16fF. Wang, S. Li, M. Qu, M.-X. Zhao, L.-J. Liu, M. Shi, Chem. Commun. 2011, 47, 12813–12815; 16gY. Wang, X. Feng, H. Du, Org. Lett. 2011, 13, 4954–4957; 16hB. Hu, M. Meng, S. Jiang, W. Deng, Chin. J. Chem. 2012, 30, 1289–1294. 17 17aE. Farrington, M. Comes-Franchini, J. M. Brown, Chem. Commun. 1998, 277–278; 17bL. Bernardi, B. F. Bonini, M. Comes-Franchini, M. Fochi, M. Folegatti, S. Grilli, A. Mazzanti, A. Ricci, Tetrahedron: Asymmetry 2004, 15, 245–250. 18For the optimization of the reaction conditions, see the Supporting Information, Table S1 and Scheme S1. 19CCDC 959849 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. 20M. Baidya, G. Y. Remennikov, P. Mayer, H. Mayr, Chem. Eur. J. 2010, 16, 1365–1371. See also the Supporting Information, Figure S1. 21 21aT. Ishimaru, N. Shibata, T. Horikawa, N. Yasuda, S. Nakamura, T. Toru, M. Shiro, Angew. Chem. 2008, 120, 4225–4229; Angew. Chem. Int. Ed. 2008, 47, 4157–4161; 21bM. H. Katcher, A. Sha, A. G. Doyle, J. Am. Chem. Soc. 2011, 133, 15902–15905; 21cE. Benedetto, M. Tredwell, C. Hollingworth, T. Khotavivattana, J. M. Brown, V. Gouverneur, Chem. Sci. 2013, 4, 89–96, and references therein. 22 22aA. T. Parsons, S. L. Buchwald, Angew. Chem. 2011, 123, 9286–9289; Angew. Chem. Int. Ed. 2011, 50, 9120–9123; 22bX. Wang, Y. Ye, S. Zhang, J. Feng, Y. Xu, Y. Zhang, J. Wang, J. Am. Chem. Soc. 2011, 133, 16410–16413; 22cY. Li, F. Liang, Q. Li, Y.-C. Xu, Q.-R. Wang, L. Jiang, Org. Lett. 2011, 13, 6082–6085; 22dL. Chu, F.-L. Qing, Org. Lett. 2012, 14, 2106–2109; 22eR. Shimizu, H. Egami, Y. Hamashima, M. Sodeoka, Angew. Chem. 2012, 124, 4655–4658; Angew. Chem. Int. Ed. 2012, 51, 4577–4580; 22fS. Mizuta, O. Galicia-López, K. M. Engle, S. Verhoog, K. Wheelhouse, G. Rassias, V. Gouverneur, Chem. Eur. J. 2012, 18, 8583–8587, and references therein. Citing Literature Volume53, Issue2January 7, 2014Pages 517-520 ReferencesRelatedInformation

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