A Highly Efficient Method for the Synthesis of Nitrogen-containing Materials Using Umpolung Addition to Electron-Deficient Imines
| Project/Area Number |
23350040
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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 | 一般 |
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| Research Field |
Synthetic chemistry
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| Research Institution | Mie University |
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Principal Investigator |
SHIMIZU Makoto 三重大学, 工学(系)研究科(研究院), 教授 (30162712)
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| Project Period (FY) |
2011-04-01 – 2014-03-31
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| Project Status |
Completed (Fiscal Year 2013)
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| Budget Amount *help |
¥19,240,000 (Direct Cost: ¥14,800,000、Indirect Cost: ¥4,440,000)
Fiscal Year 2013: ¥3,770,000 (Direct Cost: ¥2,900,000、Indirect Cost: ¥870,000)
Fiscal Year 2012: ¥5,330,000 (Direct Cost: ¥4,100,000、Indirect Cost: ¥1,230,000)
Fiscal Year 2011: ¥10,140,000 (Direct Cost: ¥7,800,000、Indirect Cost: ¥2,340,000)
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| Keywords | αーイミノエステル / 極性転換反応 / タンデム反応 / β,γ-不飽和-α-イミノエステル / α-アシロキシイミノエステル / N,N―ジアルキル化反応 / N,N.C―トリアルキル化反応 / ファインケミカルズ / β,γ-アルキニル-α-イミノエステル / N-アルキル化反応 / ビニロガスアルドール反応 / α-アミノ-δ-ラクトン / 3-アミノ2-ピロン / N,N-ジアルキル化反応 / 極性転換付加反応 / α,β‐不飽和‐α‐アミノラクトン / オキシムスルホナート / イミニウム塩 / N,N-ジアルキル化 / N,N,C-トリアルキル化 / α-イミノ酢酸エステル / 3成分カップリング反応 / イント・リン-3-オン / テトラヒドロ-4-キノロン / 有機アルミニウム試薬 / アントラニル酸メチル / アサ・-Brook転位 / トリメチルシリル酢酸エチル |
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| Research Abstract |
We have already reported that the N-alkylation reaction of alpha-iminoester proceeds using aluminum reagents to give the N-alkylation products in high yields. In the present project, we investigated highly regioselective N-alkylation of beta,gamma-alkenyl-alpha-iminoesters and subsequent directed vinylogous aldol reaction with in situ generated dienolates. It was also found that the sulfenyl group of the alkene part improved the selectivity of both steps, leading to the formation of 3-amino-2-pyrones by anti-elimination of thiols. Furthermore, on treatment with two different Grignard reagents, alpha-acyloxyimino esters gave the corresponding dialkylation products with different substituents on the nitrogen atom. N,N,C-Trialkylated products with all different substituents were obtained via the oxidation and the nucleophilic addition reaction to the resulting iminium salts.
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Report
(4 results)
Research Products
(103 results)
