2006 Fiscal Year Final Research Report Summary
Chiral Helical Polymer Ligands for Catalytic Asymmetric Synthsis with High Degree of Chiral Amplification
| Project/Area Number |
17350048
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| Research Category |
Grant-in-Aid for Scientific Research (B)
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| Allocation Type | Single-year Grants |
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| Section | 一般 |
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| Research Field |
Synthetic chemistry
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| Research Institution | Kyoto University |
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Principal Investigator |
SUGINOME Michinori Kyoto University, Faculty of Engineering, Professor (60252483)
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| Project Period (FY) |
2005 – 2006
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| Keywords | Chiral Polymer / Molecular Catalyst / Catalytic Asymmetric Synthesis / Asymmetric Polymerization / Hydrosilylation / Helical Polymer / Palladium Catalyst / Chiral Ligand |
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| Research Abstract |
New asymmetric synthesis utilizing chiral optically active polymers as chiral catalysts has been developed. New quinoxaline copolymers that possessed PPh_2 groups at their side chains and adopted right-or left-handed helical structure were synthesized through living asymmetric polymerization of 1,2-diisocyanobenzene derivatives. The optically active polymers were used as ligands in palladium-catalyzed hydrosilylation of styrene derivatives, resulting in the formation of 1-trichlorosilyl-1-phenylethane derivatives with 85-87% ee. The products were converted into optically active αphenylethyl alcohols with retention of the enantiomeric excesses. We have also developed new methods for the synthesis of oligoarene derivatives. The method relied on iterative Suzuki-Miyaura coupling reaction, in which halo-substituted arylboronic acid derivatives possessing masking groups on their boronyl groups served as coupling modules. Aiming at the application to the chiral-polymer-based asymmetric reactions, new catalytic reactions such as carboboration and silaboration of carbon-carbon unsaturated bonds have also been developed.
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Research Products
(31 results)
