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      Enantioselective Michael addition of 2-hydroxy-1,4-naphthoquinones to nitroalkenes catalyzed by binaphthyl-derived organocatalysts

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          Summary

          The highly enantioselective Michael addition of 2-hydroxy-1,4-naphthoquinones to nitroalkenes, promoted by binaphthyl-modified chiral bifunctional organocatalysts is described. This reaction afforded the chiral functionalized naphthoquinones in high yields (81–95%) and excellent enantioselectivities (91–98% ee) under low catalyst loading (1 mol %).

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          The Nitro Group in Organic Synthesis

          Noboru Ono (2001)
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            Hydrogen-bond-mediated asymmetric catalysis.

            Yan-Wei Wang, X. Yu (2008)
            The utilization of hydrogen bonding as an activation force has become a powerful tool in asymmetric organocatalysis. Significant advances have been made in the recent past in this emerging field. Due to space constraints, this Focus Review summarizes only the key aspects with an emphasis on catalysis based on chiral ureas and thioureas, diols, and phosphoric acids. The examples provided neatly demonstrate that chiral ureas and thioureas, diols, and phosphoric acids display effective and unique activation modes of catalysis for a broad spectrum of asymmetric organic transformations, including single-step and multiple-step cascade reactions. These functionalities, which have the ability to afford efficient H-bond activation of electrophiles including C=O, C=N, aziridines, and epoxides, have established their status as "privileged" functional groups in the design of organocatalysts.
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              Recent Advances in Catalytic Enantioselective Michael Additions

              Anja Hoffmann‐Röder, Norbert Krause (2001)
              Article 0 comments Cited 99 times – based on 0 reviews     Review now
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                Author and article information

                Contributors
                Dae Young Kim
                Benjamin List: Role: Guest Editor
                Journal
                Journal ID (nlm-ta): Beilstein J Org Chem
                Journal ID (iso-abbrev): Beilstein J Org Chem
                Title: Beilstein Journal of Organic Chemistry
                Publisher: Beilstein-Institut (Trakehner Str. 7-9, 60487 Frankfurt am Main, Germany )
                ISSN (Electronic): 1860-5397
                Publication date Collection: 2012
                Publication date (Electronic): 7 May 2012
                Volume: 8
                Pages: 699-704
                Affiliations
                [1 ]Department of Chemistry, Soonchunhyang University, Asan, Chungnam, 336-745, Korea
                Article
                DOI: 10.3762/bjoc.8.78
                PMC ID: 3388856
                PubMed ID: 23015816
                SO-VID: be1c6199-ee79-4b56-954e-f9d362e50c5a
                Copyright © Copyright © 2012, Woo and Kim; licensee Beilstein-Institut.
                License:

                This is an Open Access article under the terms of the Creative Commons Attribution License ( http://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

                The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: ( http://www.beilstein-journals.org/bjoc)

                History
                Date received : 7 March 2012
                Date accepted : 17 April 2012
                Categories
                Subject: Letter
                Subject: Chemistry
                Subject: Organic Chemistry

                ScienceOpen disciplines: Organic & Biomolecular chemistry
                Keywords: asymmetric catalysis,michael addition,1,4-naphthoquinones,nitroalkenes,organocatalysis
                Data availability:
                ScienceOpen disciplines: Organic & Biomolecular chemistry
                Keywords: asymmetric catalysis, michael addition, 1,4-naphthoquinones, nitroalkenes, organocatalysis

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