| Project/Area Number |
07640790
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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 |
物質変換
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| Research Institution | Kochi University |
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Principal Investigator |
KIYOOKA Syun-ichi Kochi University, Department of Chemistry, Professor, 理学部, 教授 (00036584)
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| Project Period (FY) |
1995 – 1996
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| Project Status |
Completed (Fiscal Year 1996)
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| Budget Amount *help |
¥2,200,000 (Direct Cost: ¥2,200,000)
Fiscal Year 1996: ¥200,000 (Direct Cost: ¥200,000)
Fiscal Year 1995: ¥2,000,000 (Direct Cost: ¥2,000,000)
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| Keywords | asymmetic / enantioselective / diastereoselective / aldol reaction / chiral Lewis acid / chiral borane / 1,2-diol / 1,3-diol / ジオール不斉合成 / シン・アンチ 1,2-ジオール / シン・アンチ 1,3-ジオール |
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| Research Abstract |
A study on a complete diastereo- and enantioselective synthesis of 1,2- and 1,3-diols has been developed by using our oxazaborolidinone-promoted asymmetric aldol reaction. The stereoselective construction of acyclic systems involving chiral centers was not affected by the stereochemistry of the substrates used in the reaction. This is a novel example of "catalyst control". When such a reaction is repeated, we can get a new strategy of constructing complete controlled diastereoisomers. In order to confirm the effectiveness of the strategy, we chose a mevinic acid lactone derivative of HMG-CoA reductase inhibitors, involving a syn-1,3-diol unit. Our chiral oxazaborolidinone-promoted aldol reaction of 4-phenylbutanal with a silyl ketene acetal containing a dithiolane which allows the production of the corresponding acetate aldol with the level of almost complete enantioselectivity. The second aldol reaction of the aldehyde derived from the first aldol gave the expected syn-1,3-diol by the same catalytic system. The mevinic lactone derivative was very easily synthesized. This is an excellent example of enantioselective acyclic stereoselection under catalyst control.
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