Design of Chiral Bifunctional Dialkyl Sulfide Catalysts for Regio‐, Diastereo‐, and Enantioselective Bromolactonization
Although a wide variety of chiral organocatalysts have been developed for asymmetric transformations, effective chiral dialkyl sulfide organocatalysts remain relatively rare and under‐developed, despite the potential utility of dialkyl sulfide catalysts. Herein, we report the development of chiral b...
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Published in | Chemistry : a European journal Vol. 24; no. 63; pp. 16747 - 16752 |
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Main Authors | , , , , , |
Format | Journal Article |
Language | English |
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13.11.2018
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Abstract | Although a wide variety of chiral organocatalysts have been developed for asymmetric transformations, effective chiral dialkyl sulfide organocatalysts remain relatively rare and under‐developed, despite the potential utility of dialkyl sulfide catalysts. Herein, we report the development of chiral bifunctional dialkyl sulfide catalysts possessing a urea moiety for regio‐, diastereo‐, and enantioselective bromolactonization. The importance of the bifunctional design of chiral sulfide catalysts was clearly demonstrated in the present work. The roles of both the sulfide and urea moieties of the catalyst were clarified based on the results of experimental and theoretical investigation.
Chiral bifunctional dialkyl sulfide catalysts bearing a urea moiety were designed for enantioselective bromolactonization. The roles of both sulfide and urea moieties on the catalyst are discussed and clarified based on the results of both experimental and theoretical investigation. |
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AbstractList | Although a wide variety of chiral organocatalysts have been developed for asymmetric transformations, effective chiral dialkyl sulfide organocatalysts remain relatively rare and under‐developed, despite the potential utility of dialkyl sulfide catalysts. Herein, we report the development of chiral bifunctional dialkyl sulfide catalysts possessing a urea moiety for regio‐, diastereo‐, and enantioselective bromolactonization. The importance of the bifunctional design of chiral sulfide catalysts was clearly demonstrated in the present work. The roles of both the sulfide and urea moieties of the catalyst were clarified based on the results of experimental and theoretical investigation. Abstract Although a wide variety of chiral organocatalysts have been developed for asymmetric transformations, effective chiral dialkyl sulfide organocatalysts remain relatively rare and under‐developed, despite the potential utility of dialkyl sulfide catalysts. Herein, we report the development of chiral bifunctional dialkyl sulfide catalysts possessing a urea moiety for regio‐, diastereo‐, and enantioselective bromolactonization. The importance of the bifunctional design of chiral sulfide catalysts was clearly demonstrated in the present work. The roles of both the sulfide and urea moieties of the catalyst were clarified based on the results of experimental and theoretical investigation. Although a wide variety of chiral organocatalysts have been developed for asymmetric transformations, effective chiral dialkyl sulfide organocatalysts remain relatively rare and under‐developed, despite the potential utility of dialkyl sulfide catalysts. Herein, we report the development of chiral bifunctional dialkyl sulfide catalysts possessing a urea moiety for regio‐, diastereo‐, and enantioselective bromolactonization. The importance of the bifunctional design of chiral sulfide catalysts was clearly demonstrated in the present work. The roles of both the sulfide and urea moieties of the catalyst were clarified based on the results of experimental and theoretical investigation. Chiral bifunctional dialkyl sulfide catalysts bearing a urea moiety were designed for enantioselective bromolactonization. The roles of both sulfide and urea moieties on the catalyst are discussed and clarified based on the results of both experimental and theoretical investigation. |
Author | Tsuchihashi, Ayano Mochizuki, Ayaka Kaneko, Kazuma Shirakawa, Seiji Nishiyori, Ryuichi Yamanaka, Masahiro |
Author_xml | – sequence: 1 givenname: Ryuichi surname: Nishiyori fullname: Nishiyori, Ryuichi organization: Nagasaki University – sequence: 2 givenname: Ayano surname: Tsuchihashi fullname: Tsuchihashi, Ayano organization: Nagasaki University – sequence: 3 givenname: Ayaka surname: Mochizuki fullname: Mochizuki, Ayaka organization: Rikkyo University – sequence: 4 givenname: Kazuma surname: Kaneko fullname: Kaneko, Kazuma organization: Rikkyo University – sequence: 5 givenname: Masahiro surname: Yamanaka fullname: Yamanaka, Masahiro email: myamanak@rikkyo.ac.jp organization: Rikkyo University – sequence: 6 givenname: Seiji orcidid: 0000-0003-1027-8922 surname: Shirakawa fullname: Shirakawa, Seiji email: seijishirakawa@nagasaki-u.ac.jp organization: Nagasaki University |
BackLink | https://www.ncbi.nlm.nih.gov/pubmed/30203864$$D View this record in MEDLINE/PubMed |
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Keywords | ORGANIC-SYNTHESIS SULFUR YLIDES HYDRANGEAE DULCIS FOLIUM PHASE-TRANSFER CATALYST OLEFINIC 1,3-DIOLS lactonizations organocatalysis ALKENES asymmetric synthesis transition states ASYMMETRIC EPOXIDATION SULFONIUM YLIDES YLIDE-MEDIATED EPOXIDATION sulfides REGIOSELECTIVE BROMOCYCLIZATION |
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Snippet | Although a wide variety of chiral organocatalysts have been developed for asymmetric transformations, effective chiral dialkyl sulfide organocatalysts remain... Abstract Although a wide variety of chiral organocatalysts have been developed for asymmetric transformations, effective chiral dialkyl sulfide organocatalysts... |
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SubjectTerms | asymmetric synthesis Catalysis Catalysts Chemistry Chemistry, Multidisciplinary Dialkyl sulfides Enantiomers lactonizations organocatalysis Physical Sciences Science & Technology Sulfide Sulfides transition states Urea Ureas |
Title | Design of Chiral Bifunctional Dialkyl Sulfide Catalysts for Regio‐, Diastereo‐, and Enantioselective Bromolactonization |
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