2002 Fiscal Year Final Research Report Summary
Development and Application of Novel Asymmetric Carbon-Carbon Bond Forming Reactions
| Project/Area Number |
13672224
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| Research Category |
Grant-in-Aid for Scientific Research (C)
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| Allocation Type | Single-year Grants |
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| Section | 一般 |
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| Research Field |
Chemical pharmacy
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| Research Institution | University of Shizuoka |
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Principal Investigator |
TANAKA Kiyoshi University of Shizuoka, School of Pharmaceutical Sciences, Professor, 薬学部, 教授 (50093266)
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| Project Period (FY) |
2001 – 2002
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| Keywords | Asymmetric tandem reaction / One-flask reaction / Multiple asymmetric induction / Successive multi-component reaction / Asymmetric Michael reaction / Asymmetric olefination / Dynamic kinetic resolution |
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| Research Abstract |
Control of carbon skeleton including stereochemistry is a major factor for construction of useful and complex organic molecules. This study is involves in such a research work whose contents is development of novel and unique tantem carbon-carbon bond forming reactions of multi-components. The results and useful information obtained from this research work will be reviewed below.
A combination of the Wittig and Michael reactions was designed for a new tandem reaction system and first function of two binaphthyl derivative was examined for effective substrate. A preliminary experiment of the asymmetric Michael reaction was carried out to give a high stereo(enantio) selectivity. Successively, the tandem Michael and HWE reaction was next tried using benzaldehyde as trapping substrate of the in situ generated carbanion giving the product with quite high enantioselectivity. This one-flask tandem reaction was successfully applied to double asymmetric induction. The ability of newly designed HWE reagent was investigated in three kinds of effective approaches for asymmetric olefination and the product formation with high both the chemical and optical yields was observed.
Finally, the tandem asymmetric Michael-HWE system was efficiently applied to dynamic kinetic resolution to give the product in satisfactory chemical yield with high diastereo-selectivity.
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