Studies on synthesis of heterocycles and carbocycles by sequential reactions using unsaturated esters
| Project/Area Number |
23550054
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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) |
2011 – 2013
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| Project Status |
Completed (Fiscal Year 2013)
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| Budget Amount *help |
¥5,200,000 (Direct Cost: ¥4,000,000、Indirect Cost: ¥1,200,000)
Fiscal Year 2013: ¥910,000 (Direct Cost: ¥700,000、Indirect Cost: ¥210,000)
Fiscal Year 2012: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
Fiscal Year 2011: ¥2,340,000 (Direct Cost: ¥1,800,000、Indirect Cost: ¥540,000)
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| Keywords | 合成反応 / 効率的結合形成 / ルイス酸 / 不飽和エステル / α,β-不飽和エステル / エテントリカルボン酸 / テトラヒドロフラン / ピロリジン / ヘテロ環 / アルケニルエステル / 立体選択的合成 / アリルエステル / エテントリカルボン酸エステル / アゾジカルボン酸エステル / トリフェニルホスフィン / ジアリールアレン / 塩化スズ / ビニルケトン / インデン |
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| Research Abstract |
New efficient cyclization reactions using highly reactive alfa,beta-unsaturated esters by sequential bond formations has been developed.
The reaction of unsaturated esters such as ethenetricarboxylates, 2-phosphonoacrylate and 2-(trifluoromethyl)acrylate with diethyl azodicarboxylate and PPh3 gave pyrazolines efficiently. Reaction of allyl ethenetricarboxylates and the amides with Lewis acids such as TiCl4, TiBr4 and AlCl3 gave 3,4-trans-halogenomethyl 2-oxotetrahydrofuran and pyrrolidine derivatives stereoselectively in high yields. The stereochemistries were determined by NOE experiments. Reaction of (E)/(Z)-2-butenyl esters with AlCl3 or FeCl3 gave 3,4-trans 4-(1-chloroethyl) tetrahydro-2-oxofuran diastereoisomers stereospecifically. Reaction of (E)/(Z)-2-butenyl and 2-pentenyl amides with ZnI2 gave 3,4-trans 4-(1-iodoethyl and propyl) tetrahydro-2-oxopyrrolidine diastereoisomers stereospecifically.
These reactions represent efficient ways to construct potentially useful compounds.
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Report
(4 results)
Research Products
(43 results)
