2007 Fiscal Year Final Research Report Summary
New Development of Organic Syntheses mediated by Functional Allene Intermediates
| Project/Area Number |
18590021
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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 | Meijo University |
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Principal Investigator |
SHIOIRI Takayuki Meijo University, Graduate School of Environmental & Human Sciences, Adjunct Professor (20012627)
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| Co-Investigator(Kenkyū-buntansha) |
ITO Mikio Meijo University, Faculty of Pharmacy, Professor (60076726)
MORI Yuji Meijo University, Faculty of Pharmacy, Professor (40121511)
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| Project Period (FY) |
2006 – 2007
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| Keywords | β-substituted Morita-Baylis-Hillman type compound / (Z)-chalcone / siloxyallene intermediates / potassium tert-butoxide / カリウムtert-ブトキシド |
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| Research Abstract |
We have already developed a new tandem addition-isomerization-sily1 aldol reaction of aromatic aldehydes with phenyltrimethylsilylacetylene catalyzed by a quaternary ammonium fluoride derived from cinchonine, giving (Z)-β-substituted Morita-Baylis-Hillman type compounds via siloxyallenes as functional allenes. As an extension of this reaction, treatment of O-trimethylsily1 derivatives of propargyl alcohols having the aromatic functions at the both terminals with potassium tertbutoxide was found to produce siloxyallene intermediates, which react with various aldehydes to furnish (Z)-β-substituted Morita-Baylis-Hillman type compounds. This reaction will be called a tandem isomerization-silylaldol reaction. In place of aldehydes, treatment of siloxyallene intermediates with sulfuric acid stereoselectively affords (Z)-chalcones. The siloxyallene intermediates will be expected to produce a variety of (Z)-β-substituted Morita-Baylis-Hillman type compounds by the reaction with the other electrophiles.
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