Direct Enantioselective Amination of α‐Ketoesters Catalyzed by an Axially Chiral Guanidine Base
2011; Wiley; Volume: 17; Issue: 33 Linguagem: Inglês
10.1002/chem.201101076
ISSN1521-3765
AutoresMasahiro Terada, Kei Amagai, Kenichi Ando, Eunsang Kwon, Hitoshi Ube,
Tópico(s)Synthesis and Catalytic Reactions
ResumoChemistry – A European JournalVolume 17, Issue 33 p. 9037-9041 Communication Direct Enantioselective Amination of α-Ketoesters Catalyzed by an Axially Chiral Guanidine Base Correction(s) for this article Corrigendum: Direct Enantioselective Amination of α-Ketoesters Catalyzed by an Axially Chiral Guanidine Base Masahiro Terada, Kei Amagai, Kenichi Ando, Eunsang Kwon, Hitoshi Ube, Volume 17Issue 36Chemistry – A European Journal pages: 9858-9858 First Published online: August 22, 2011 Prof. Dr. Masahiro Terada, Corresponding Author Prof. Dr. Masahiro Terada [email protected] Department of Chemistry, Graduate School of Science, Tohoku University, Aramaki, Aoba-ku, Sendai 980-8578 (Japan), Fax: (+81) 22-795-6602 http://www.orgreact.sakura.ne.jp/index.html Research and Analytical Center for Giant Molecules, Graduate School of Science, Tohoku University, Aramaki, Aoba-ku, Sendai 980-8578 (Japan)Department of Chemistry, Graduate School of Science, Tohoku University, Aramaki, Aoba-ku, Sendai 980-8578 (Japan), Fax: (+81) 22-795-6602 http://www.orgreact.sakura.ne.jp/index.htmlSearch for more papers by this authorKei Amagai, Kei Amagai Department of Chemistry, Graduate School of Science, Tohoku University, Aramaki, Aoba-ku, Sendai 980-8578 (Japan), Fax: (+81) 22-795-6602 http://www.orgreact.sakura.ne.jp/index.htmlSearch for more papers by this authorKenichi Ando, Kenichi Ando Department of Chemistry, Graduate School of Science, Tohoku University, Aramaki, Aoba-ku, Sendai 980-8578 (Japan), Fax: (+81) 22-795-6602 http://www.orgreact.sakura.ne.jp/index.htmlSearch for more papers by this authorDr. Eunsang Kwon, Dr. Eunsang Kwon Research and Analytical Center for Giant Molecules, Graduate School of Science, Tohoku University, Aramaki, Aoba-ku, Sendai 980-8578 (Japan)Search for more papers by this authorDr. Hitoshi Ube, Dr. Hitoshi Ube Department of Chemistry, Graduate School of Science, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan)Search for more papers by this author Prof. Dr. Masahiro Terada, Corresponding Author Prof. Dr. Masahiro Terada [email protected] Department of Chemistry, Graduate School of Science, Tohoku University, Aramaki, Aoba-ku, Sendai 980-8578 (Japan), Fax: (+81) 22-795-6602 http://www.orgreact.sakura.ne.jp/index.html Research and Analytical Center for Giant Molecules, Graduate School of Science, Tohoku University, Aramaki, Aoba-ku, Sendai 980-8578 (Japan)Department of Chemistry, Graduate School of Science, Tohoku University, Aramaki, Aoba-ku, Sendai 980-8578 (Japan), Fax: (+81) 22-795-6602 http://www.orgreact.sakura.ne.jp/index.htmlSearch for more papers by this authorKei Amagai, Kei Amagai Department of Chemistry, Graduate School of Science, Tohoku University, Aramaki, Aoba-ku, Sendai 980-8578 (Japan), Fax: (+81) 22-795-6602 http://www.orgreact.sakura.ne.jp/index.htmlSearch for more papers by this authorKenichi Ando, Kenichi Ando Department of Chemistry, Graduate School of Science, Tohoku University, Aramaki, Aoba-ku, Sendai 980-8578 (Japan), Fax: (+81) 22-795-6602 http://www.orgreact.sakura.ne.jp/index.htmlSearch for more papers by this authorDr. Eunsang Kwon, Dr. Eunsang Kwon Research and Analytical Center for Giant Molecules, Graduate School of Science, Tohoku University, Aramaki, Aoba-ku, Sendai 980-8578 (Japan)Search for more papers by this authorDr. Hitoshi Ube, Dr. Hitoshi Ube Department of Chemistry, Graduate School of Science, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan)Search for more papers by this author First published: 12 July 2011 https://doi.org/10.1002/chem.201101076Citations: 36Read 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 β-functional! Direct enantioselective amination of α-ketoesters with azodicarboxylates was demonstrated using an axially chiral guanidine base catalyst, which enabled efficient access to enantioenriched multifunctionalized ketoesters with an aliphatic substituent at the β-position. Subsequent nucleophilic addition to the β-hydrazinyl-α-ketoester at the reactive ketone yields the corresponding β-hydrazinyl-α-hydroxy esters in high syn diastereo- and enantioselectivities (see scheme). 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 chem_201101076_sm_miscellaneous_information.pdf1,004.2 KB 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 a recent review, see: M. Shibasaki, M. Kanai, Chem. Rev. 2008, 108, 2853–2873. 2For selected examples, see: 2aD. A. Evans, M. C. Kozlowski, C. S. Burgey, D. W. C. MacMillan, J. Am. Chem. Soc. 1997, 119, 7893–7894; 2bD. A. Evans, D. W. C. MacMillan, K. R. Campos, J. Am. Chem. Soc. 1997, 119, 10859–10860; 2cM. Johannsen, S. Yao, K. A. Jørgensen, Chem. Commun. 1997, 2169–2170; 2dS. Yao, M. Johannsen, H. Audrain, R. G. Hazell, K. A. Jørgensen, J. Am. Chem. Soc. 1998, 120, 8599–8605; 2eD. A. Evans, S. W. Tregay, C. S. Burgey, N. A. Paras, T. Vojkovsky, J. Am. Chem. Soc. 2000, 122, 7936–7943; 2fH. Audrain, K. A. Jørgensen, J. Am. Chem. 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Asian J. 2009, 4, 488–507. 11Epimerization of 4 was observed during purification by silica-gel column chromatography. 12When the reaction was performed using 5 mol % of (R)-3 h in THF at 0 °C for 23 h, the corresponding product 7 was obtained in moderate yield (50 %) with low enantioselectivity (27 % ee). 13M. Hatano, S. Suzuki, K. Ishihara, J. Am. Chem. Soc. 2006, 128, 9998–9999. 14CCDC-722240 ([(R)-3 i⋅H]+BF4−) contains the supplementary crystallographic data for this paper. This data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif. 15An essentially identical result was obtained from the Mulliken population analysis, which indicates that the N1 atom is more positive than the N2 atom. See the Supporting Information for details. 16The relative stabilities of the enol forms of 1 were evaluated by DFT calculations at the B3LYP/6-311+g(d,p) level. The Z isomer is more stable than the E isomer by 3.98 kcal mol−1. See the Supporting Information for details of the computational studies. 17 17aE. J. Corey, M. J. Grogan, Org. Lett. 1999, 1, 157–160; 17bZ. Jiang, Y. Pan, Y. Zhao, T. Ma, R. Lee, Y. Yang, K.-W. Huang, M. W. Wong, C.-H. Tan, Angew. Chem. 2009, 121, 3681–3685; Angew. Chem. Int. Ed. 2009, 48, 3627–3631. Citing Literature Volume17, Issue33August 8, 2011Pages 9037-9041 ReferencesRelatedInformation
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