1999 Fiscal Year Final Research Report Summary
The Establishment and Application of Simple Catalytic Preparation of High Optical Active Chiral Compounds
| Project/Area Number |
10554037
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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 | 展開研究 |
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| Research Field |
Organic chemistry
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| Research Institution | Yamaguchi University |
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Principal Investigator |
OGUNI Nobuki Department of Chemistry and Earth Science, Yamaguchi University Professor of Chemistry,, 理学部, 教授 (60028165)
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| Co-Investigator(Kenkyū-buntansha) |
HARADA Katsumasa Ube Chemical Ind. Ube Institute, Research Manager,, 有機合成部長
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| Project Period (FY) |
1998 – 1999
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| Keywords | Aldehyde / Diketene / Enantioselective reaction / Chiral schiff base / Titanium complex / Cholesterol / Optical active product / 光学活性化合物 |
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| Research Abstract |
The reaction of aldehydes with diketene is known to give 5-hdroxy-3-ketoesters by Lewis acid catalyst like TiClィイD24ィエD2. But the products in this reaction are racemic mixture and the reaction of cinnamic aldehyde with diketene did not give addition product. The author obtained the products in high yield using Ti(OiPr)ィイD24ィエD2 as catalyst. Also we found the above enantioselective reaction catalyzed by chiral schiff base-titanium complexes which were very effective for the asymmetric reaction of aldehydes with trimethylsilyl cyanide. In this reaction the some optically active product become precursor of synthetic drugs, particularly active for lowering cholesterol. The results of optimization research afforded the reaction conditions giving 90% ee's product in good yield. Also in the use of 20 mol% of the chiral catalist gave the product in good enantio-selectivity only in use of an equimolar amount of Ti(OiPr)ィイD24ィエD2. The recovery of the chiral catalyst was accomplished by cationic resins such as Dowex which was revailed by the research in Ube Chemical Institute.
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