1991 Fiscal Year Final Research Report Summary
Asymmetric Reaction of ferrocene Derivatives Using Microbe or Enzyme.
| Project/Area Number |
02640377
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| Research Category |
Grant-in-Aid for General Scientific Research (C)
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| Allocation Type | Single-year Grants |
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| Research Field |
有機化学一般
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| Research Institution | Yamagata University |
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Principal Investigator |
IZUMI Taeko Yamagata University, Faculty of Engineering, Associate Professor., 工学部, 助教授 (10007031)
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| Project Period (FY) |
1990 – 1991
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| Keywords | Chiral ferrocene compound / Baker's yeast / Lipase / Planar chiral compound / Enantioselective reduction / Enantioselective transesterification |
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| Research Abstract |
The application of biocatalytic reaction to organic synthesis has been shown to be a Tiighly pratical and efficient means of preparing chiral molecules. The value of organometallic compoundd in modern organic synthesis has also been widely recognised, and a combination of organometallic and enzymatic chemistries of offers great potential. Ferrocene compounds which have two different substituents on the same ring are optically active compounds having planer chirality. We have invastigated microbial or enzymatic transformation reaction of these recemic ferrocene compounds, which have been done to survey what microorganisms can react enantioselectively to these planar chirality compounds, and secondly to f ind the some regularity in this reaction about influence of substituents position and reaction condition. Three kinds of reaction, baker's yeast reduction, transesterification or hydrolysis reaction with lipase have been performed. Twenty five ferrocene 1, 2- or 1, 3-disubstituted ferro
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cene compounds are synthesized as the substrates. Racemic 2- or 3-substituted derivatives of formylferrocene were kinetically resolved by enantioselective reduction with a fermenting baker's yeast. Moreover, 2- or 3-substituted derivatives of hydroxymethyl ferrocene were optically resolved with lipases by transesterification using vinyl esters in organic solvent(hexane or diisopropyl ether). In the microbial asymmetric reduction of ferrocene aldehyde with baker's yeast, planar chiral alcohol are obtained as opposite absolute configuration on different substituents position 2- and 3-. In the transesterification of hydroxymethyl ferrocene derivatives with lipase, optically purity of products depends of the substituent size despite of longer reaction time. Chiral ferrocene compounds having high optical purity are possible to obtained by using the most suitable combination of condition(enzyme, acylation reagent, and solvent). All the products of these microbial reaction are explained by Prelog's or Quadrant's rule. Less
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Research Products
(8 results)
