2016 Fiscal Year Final Research Report
Selective synthesis of heterocycles and carbocycles by alkene cyclization via conjugate addition as a key reaction
| Project/Area Number |
26410048
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| Research Category |
Grant-in-Aid for Scientific Research (C)
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| Allocation Type | Multi-year Fund |
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| Section | 一般 |
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| Research Field |
Organic chemistry
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| Research Institution | Nara University of Education |
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Principal Investigator |
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| Project Period (FY) |
2014-04-01 – 2017-03-31
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| Keywords | 共役付加 / ヘテロ環 / 環化反応 / ルイス酸 / エテントリカルボン酸 / 分子内環化付加 / 立体選択性 |
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| Outline of Final Research Achievements |
Selective synthesis of heterocycles by alkene cyclization of ethenetricarboxylates via conjugate addition has been studied. Reaction of E/Z-2-alkenyl esters and amides of ethenetricarboxylate with Lewis acids gave 2-oxotetrahydrofuran and pyrrolidine diastereomers stereospecifically. Sc(OTf)3-catalyzed cyclization of the allyl amides gave 2-oxopyrrolidine derivatives efficiently.
Reaction of 2-hydrogen ethenetricarboxylate and E-cinnamylamines under the amide formation conditions led to pyrrolidine products in one pot, via intramolecular [2+2] and [4+2] cyclizations, depending on the substituents and the reaction conditions. Reaction with Z-cinnamylamines gave cis-fused tricyclic compounds via amide formation/[4+2] cyclization. The reactions with 3,3-diaryl-2-propenylamines gave cis- and trans-fused tricyclic compounds selectively, depending on the substituents, temperature and solvent.
The cyclized products may be transformed to potentially useful compounds.
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| Free Research Field |
有機合成化学
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