Synthetic Study of Functionalized Amino Acids Using An Umpolung Addition to α-Imino Esters
| Project/Area Number |
20350047
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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 Mie University, 大学院・工学研究科, 教授 (30162712)
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| Co-Investigator(Kenkyū-buntansha) |
HACHIYA Iwao 三重大学, 大学院・工学研究科, 准教授 (50312038)
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| Project Period (FY) |
2008 – 2010
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| Project Status |
Completed (Fiscal Year 2010)
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| Budget Amount *help |
¥19,890,000 (Direct Cost: ¥15,300,000、Indirect Cost: ¥4,590,000)
Fiscal Year 2010: ¥3,250,000 (Direct Cost: ¥2,500,000、Indirect Cost: ¥750,000)
Fiscal Year 2009: ¥4,940,000 (Direct Cost: ¥3,800,000、Indirect Cost: ¥1,140,000)
Fiscal Year 2008: ¥11,700,000 (Direct Cost: ¥9,000,000、Indirect Cost: ¥2,700,000)
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| Keywords | α-イミノエステル / α-アミノエステル / 極性転換反応 / イミニウム塩 / 含窒素化合物 / 付加反応 / 官能基選択性 / Friedel-Crafts反応 / マンニッヒ反応 / ジアステレオ選択性 / イミノマロネート / アミノジエステル / エン反応 / α-アミノ酢酸エステル / ケテンシリルアセタール / シリルエノールエーテル / インドール / タンデム付加体 / α-イミノ酢酸エステル / 3成分カップリング反応 / 極性転換付加反応 / グリオキシル酸エステル / N-アルキル化反応 / アミノベンゾニトリル / インドリン |
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| Research Abstract |
α-Imino esters behave as acceptors of nucleophiles at their nitrogen atoms in an "umpoled" manner, when appropriate nucleophiles are used. The tandem N-alkylation-C-allylation and N-alkylation-C-cyanation reaction of several α-imino esters with organoaluminums are carried out in good to excellent yields, where two nucleophiles attack across the C=N double bond. Moreover, three components coupling reaction of α-imino ester derived from ethyl glyoxylate, aluminum reagent, and various electrophiles proceeded to give the addition products in good yields. The alkoxycarbonyl iminium salt is easily prepared using the oxidation of amino ketene silyl acetal, and subsequent nucleophilic addition to this iminium species proceeds efficiently to afford the α-amino esters in good yields.
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Report
(4 results)
Research Products
(93 results)
