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      Dinuclear PhosphoiminoBINOL-Pd Container for Malononitrile: Catalytic Asymmetric Double Mannich Reaction for Chiral 1,3-Diamine Synthesis

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          Abstract

          A phosphoiminoBINOL ligand was designed to form a dinuclear metal complex that could hold a malononitrile molecule. The dinuclear bis(phosphoimino)binaphthoxy-Pd 2(OAc) 2 complex catalyzed a double Mannich reaction of N-Boc-imines with malononitrile to give chiral 1,3-diamines with high enantioselectivity. The rational asymmetric catalyst, which smoothly introduces the first coupling product to the second coupling reaction while avoiding the reverse reaction, facilitates the over-reaction into a productive reaction process.

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          Enantioselective Michael additions to alpha,beta-unsaturated imides catalyzed by a Salen-Al complex.

          N Jacobsen, Susan S. Taylor (2003)
          (Salen)aluminum complex 1b is an efficient catalyst for the conjugate addition of di- and trisubstituted nitriles to a wide range of acyclic alkyl- and aryl-substituted alpha,beta-unsaturated imides. This new methodology provides access to multifunctional compounds that previously have not been readily accessible in enantioenriched form. Synthetic applications of these products include the preparation of enantiomerically enriched piperidines, as exemplified by an expedient asymmetric catalytic synthesis of (-)-paroxetine.
          Article 0 comments Cited 51 times – based on 0 reviews     Review now
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            Dinuclear {(salen)Al} Complexes Display Expanded Scope in the Conjugate Cyanation of α,β-Unsaturated Imides

            Eric Jacobsen, Clément Mazet (2008)
            Article 0 comments Cited 43 times – based on 0 reviews     Review now
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              Linking structural dynamics and functional diversity in asymmetric catalysis.

              Akihiro Nojiri, Naoya Kumagai, Masakatsu Shibasaki (2009)
              Proteins, the functional molecules in biological systems, are sophisticated chemical devices that have evolved over billions of years. Their function is intimately related to their three-dimensional structure and elegantly regulated by conformational changes through allosteric regulators and a number of reversible or unidirectional post-translational modifications. This functional diversification in response to external stimuli allows for an orderly and timely progression of intra- and extracellular events. In contrast, enantioselective catalysts generally exhibit limited conformational flexibility and thereby exert a single specific function. Exploiting the features of conformationally flexible asymmetric ligands and the variable coordination patterns of rare earth metals, we demonstrate dynamic structural and functional changes of a catalyst in asymmetric catalysis, leading to two distinct reaction outcomes in a single flask.
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                Author and article information

                Contributors
                Takayoshi Arai:
                ORCID: http://orcid.org/0000-0001-9490-3988
                tarai@faculty.chiba-u.jp
                Journal
                Journal ID (nlm-ta): Sci Rep
                Journal ID (iso-abbrev): Sci Rep
                Title: Scientific Reports
                Publisher: Nature Publishing Group UK (London )
                ISSN (Electronic): 2045-2322
                Publication date (Electronic): 16 January 2018
                Publication date PMC-release: 16 January 2018
                Publication date Collection: 2018
                Volume: 8
                Electronic Location Identifier: 837
                Affiliations
                [1 ]ISNI 0000 0004 0370 1101, GRID grid.136304.3, Soft Molecular Activation Research Center (SMARC), , Graduate School of Science, Chiba University, 1-33 Yayoi, ; Inage Chiba, 263-8522 Japan
                [2 ]ISNI 0000 0004 0370 1101, GRID grid.136304.3, Molecular Chirality Research Center (MCRC), , Graduate School of Science, Chiba University, 1-33 Yayoi, ; Inage Chiba, 263-8522 Japan
                [3 ]ISNI 0000 0004 0370 1101, GRID grid.136304.3, Department of Chemistry, , Graduate School of Science, Chiba University, 1-33 Yayoi, ; Inage Chiba, 263-8522 Japan
                [4 ]ISNI 0000 0004 0370 1101, GRID grid.136304.3, Center for Analytical Instrumentation, , Chiba University, 1-33 Yayoi, ; Inage Chiba, 263-8522 Japan
                Author information
                http://orcid.org/0000-0001-9490-3988
                Article
                Publisher ID: 19178
                DOI: 10.1038/s41598-018-19178-4
                PMC ID: 5770441
                PubMed ID: 29339816
                SO-VID: 4dff6061-9eb2-4e6a-a045-7bb237dd83a2
                Copyright © © The Author(s) 2018
                License:

                Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons license and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/.

                History
                Date received : 15 September 2017
                Date accepted : 22 December 2017
                Categories
                Subject: Article
                Custom metadata
                issue-copyright-statement © The Author(s) 2018

                ScienceOpen disciplines: Uncategorized
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                ScienceOpen disciplines: Uncategorized

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