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Asymmetric Neutral Amination of Nitroolefins Catalyzed by Chiral Bifunctional Ammonium Salts in Water‐Rich Biphasic Solvent

2011; Wiley; Volume: 50; Issue: 23 Linguagem: Inglês

10.1002/anie.201101307

1521-3773

Lijia Wang, Seiji Shirakawa, Keiji Maruoka,

Synthesis and Catalytic Reactions

Angewandte Chemie International EditionVolume 50, Issue 23 p. 5327-5330 Communication Asymmetric Neutral Amination of Nitroolefins Catalyzed by Chiral Bifunctional Ammonium Salts in Water-Rich Biphasic Solvent† Dr. Lijia Wang, Dr. Lijia Wang Laboratory of Synthetic Organic Chemistry and Special, Laboratory of Organocatalytic Chemistry, Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502 (Japan), Fax: (+81) 75-753-4041Search for more papers by this authorDr. Seiji Shirakawa, Dr. Seiji Shirakawa Laboratory of Synthetic Organic Chemistry and Special, Laboratory of Organocatalytic Chemistry, Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502 (Japan), Fax: (+81) 75-753-4041Search for more papers by this authorProf. Dr. Keiji Maruoka, Corresponding Author Prof. Dr. Keiji Maruoka [email protected] Laboratory of Synthetic Organic Chemistry and Special, Laboratory of Organocatalytic Chemistry, Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502 (Japan), Fax: (+81) 75-753-4041Laboratory of Synthetic Organic Chemistry and Special, Laboratory of Organocatalytic Chemistry, Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502 (Japan), Fax: (+81) 75-753-4041Search for more papers by this author Dr. Lijia Wang, Dr. Lijia Wang Laboratory of Synthetic Organic Chemistry and Special, Laboratory of Organocatalytic Chemistry, Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502 (Japan), Fax: (+81) 75-753-4041Search for more papers by this authorDr. Seiji Shirakawa, Dr. Seiji Shirakawa Laboratory of Synthetic Organic Chemistry and Special, Laboratory of Organocatalytic Chemistry, Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502 (Japan), Fax: (+81) 75-753-4041Search for more papers by this authorProf. Dr. Keiji Maruoka, Corresponding Author Prof. Dr. Keiji Maruoka [email protected] Laboratory of Synthetic Organic Chemistry and Special, Laboratory of Organocatalytic Chemistry, Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502 (Japan), Fax: (+81) 75-753-4041Laboratory of Synthetic Organic Chemistry and Special, Laboratory of Organocatalytic Chemistry, Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502 (Japan), Fax: (+81) 75-753-4041Search for more papers by this author First published: 28 April 2011 https://doi.org/10.1002/anie.201101307Citations: 74 † This work was supported by a Grant-in-Aid for Scientific Research from the MEXT (Japan) and The Association for the Progress of New Chemistry. We are grateful to Dr. Hiroyasu Sato (Rigaku Corporation) for X-ray crystallographic analysis. 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 It′s just a phase: Environmentally benign title reaction was achieved under neutral phase-transfer conditions in the presence of 0.05 mol % of a chiral bifunctional ammonium bromide. The importance of bifunctional design of the chiral phase-transfer catalysts (PTC) was clearly shown in the transition-state model of the reaction based on the single-crystal X-ray structure. Bn=benzyl, Boc=tert-butoxycarbonyl. Supporting Information Detailed facts of importance to specialist readers are published as "Supporting Information". Such documents are peer-reviewed, but not copy-edited or typeset. They are made available as submitted by the authors. Filename Description anie_201101307_sm_miscellaneous_information.pdf6.9 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 1For representative reviews on asymmetric organocatalysis, see: 1aP. I. Dalko, L. Moisan, Angew. Chem. 2004, 116, 5248; Angew. Chem. Int. Ed. 2004, 43, 5138; 1bJ. Seayad, B. List, Org. 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Tomás, Tetrahedron Lett. 1980, 21, 3709. 7Phase-transfer catalyzed asymmetric cyclizations with nitrogen nucleophiles: 7aJ. Aires-de-Sousa, A. M. Lobo, S. Prabhakar, Tetrahedron Lett. 1996, 37, 3183; 7bJ. Aires-de-Sousa, S. Prabhakar, A. M. Lobo, A. M. Rosa, M. J. S. Gomes, M. C. Corvo, D. J. Williams, A. J. P. White, Tetrahedron: Asymmetry 2001, 12, 3349; 7cR. Fioravanti, M. G. Mascia, L. Pellacani, P. A. Tardella, Tetrahedron 2004, 60, 8073; 7dE. Murugan, A. Siva, Synthesis 2005, 2022; 7eS. Minakata, Y. Murakami, R. Tsuruoka, S. Kitanaka, M. Komatsu, Chem. Commun. 2008, 6363; 7fM. Bandini, A. Eichholzer, M. Tragni, A. Umani-Ronchi, Angew. Chem. 2008, 120, 3282; Angew. Chem. Int. Ed. 2008, 47, 3238; 7gK. Tomooka, K. Uehara, R. Nishikawa, M. Suzuki, K. Igawa, J. Am. Chem. Soc. 2010, 132, 9232; 7hO. Mahé, I. Dez, V. Levacher, J.-F. Brière, Angew. Chem. 2010, 122, 7226; Angew. Chem. Int. Ed. 2010, 49, 7072; 7iM. Bandini, A. Bottoni, A. Eichholzer, G. P. Miscione, M. Stenta, Chem. Eur. J. 2010, 16, 12462. 8Tetrabutylammonium-bromide-catalyzed conjugate amination with tert-butyl benzyloxycarbamate: J. Lee, M.-h. Kim, S.-s. Jew, H.-g. Park, B.-S. Jeong, Chem. Commun. 2008, 1932. 9R. He, S. Shirakawa, K. Maruoka, J. Am. Chem. Soc. 2009, 131, 16620. 10 10aM. Kitamura, S. Shirakawa, K. Maruoka, Angew. Chem. 2005, 117, 1573; Angew. Chem. Int. Ed. 2005, 44, 1549; 10bX. Wang, M. Kitamura, K. Maruoka, J. Am. Chem. Soc. 2007, 129, 1038; 10cM. Kitamura, S. Shirakawa, Y. Arimura, X. Wang, K. Maruoka, Chem. Asian J. 2008, 3, 1702. 11X. Wang, Q. Lan, S. Shirakawa, K. Maruoka, Chem. Commun. 2010, 46, 321. 12The BF4− and TfO− salts of (S)-2 c showed similar results to the corresponding bromide salt. 13The reaction in pure water without toluene proceeded very sluggishly owing to the low solubility of solid substrates and catalyst in water. 14Half-life of 4-TBSOC6H4Me for the hydrolysis in acidic or basic conditions: 4.6 h (1 % HCl in MeOH), 3.5 min (5 % NaOH in MeOH). J. S. Davies, C. L. Higginbotham, E. J. Tremeer, C. Brown, R. C. Treadgold, J. Chem. Soc. Perkin Trans. 1 1992, 3043. 15The absolute configuration of 7 was determined by comparison of optical rotation with reported data, see: 15aP. M. O'Brien, D. R. Sliskovic, C. J. Blankley, B. D. Roth, M. W. Wilson, K. L. Hamelehle, B. R. Krause, R. L. Stanfield, J. Med. Chem. 1994, 37, 1810; 15bB. M. Nugent, R. A. Yoder, J. N. Johnston, J. Am. Chem. Soc. 2004, 126, 3418. 16CCDC 792748 ((S)-2 d) 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. 17Hydrogen-bonding interaction between the nitrostyrene and hydroxy groups in the catalyst may also play an important role to obtain high enantioselectivity in this reaction. For hydrogen-bonding interaction between the nitro group of the substrate and the hydroxy group in the catalyst for phase-transfer reaction, see: E. Gomez-Bengoa, A. Linden, R. López, I. Múgica-Mendiola, M. Oiarbide, C. Palomo, J. Am. Chem. Soc. 2008, 130, 7955. Citing Literature Volume50, Issue23May 27, 2011Pages 5327-5330 ReferencesRelatedInformation