ultimate asymmetric synthesis of medicinal compounds by borrowing hydrogen reaction
| Project/Area Number |
26410047
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| Research Category |
Grant-in-Aid for Scientific Research (C)
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| Allocation Type | Multi-year Fund |
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| Section | 一般 |
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| Research Field |
Organic chemistry
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| Research Institution | Osaka University |
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Principal Investigator |
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| Co-Investigator(Kenkyū-buntansha) |
朝野 芳織 大阪大学, 産業科学研究所, 助教 (00311762)
周 大揚 大阪大学, 産業科学研究所, 助教 (00324848)
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| Co-Investigator(Renkei-kenkyūsha) |
SASAI Hiroaki 大阪大学, 産業科学研究所, 教授 (90205831)
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| Project Period (FY) |
2014-04-01 – 2017-03-31
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| Project Status |
Completed (Fiscal Year 2016)
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| Budget Amount *help |
¥5,070,000 (Direct Cost: ¥3,900,000、Indirect Cost: ¥1,170,000)
Fiscal Year 2016: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2015: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2014: ¥2,210,000 (Direct Cost: ¥1,700,000、Indirect Cost: ¥510,000)
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| Keywords | イリジウム / 水素借用反応 / catalponol / Tishchenko / 酸化 / 還元 / ラクトン / 非対称化 / 水素移動反応 / アルドール反応 |
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| Outline of Final Research Achievements |
Tandem asymmetric hydrogen transfer oxidation/aldol condensation under relay catalysis of a chiral iridium complex/achiral Brønsted base binary system is described for the synthesis of α-benzylidene-γ-hydroxytetralones with high ee’s. A two-step synthesis of catalponol was achieved using this sequential methodology together with regio- and stereoselective hydroboration.
Ir-catalyzed asymmetric Tishchenko type reaction has been investigated. The reaction involves a reduction step of dialdehyde,.the intramolecular cyclization and the final oxidation to form lactone. The reaction of meso-dialdehude took place selectively to give the desired lactone with 78% yield and 91% ee . This is the first example of asymmetric Tishchenko type reaction
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Report
(4 results)
Research Products
(5 results)
