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KAKEN_15K05436seika.pdf
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反応性制御素子N-アルコキシ基を用いたアミド基変換反応の自在制御
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Kana |
ハンノウセイ セイギョ ソシ N-アルコキシキ オ モチイタ アミドキ ヘンカン ハンノウ ノ ジザイ セイギョ
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Hannōsei seigyo soshi N-arukokishiki o mochiita amidoki henkan hannō no jizai seigyo
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Transformation of amides by using an N-alkoxy group as a reactivity control element
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佐藤, 隆章
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サトウ, タカアキ
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Sato, Takaaki
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慶應義塾大学・理工学部・准教授
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Research team head
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科研費研究者番号 : 70509926
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2018
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科学研究費補助金研究成果報告書
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2017
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2つのヘテロ原子が結合すると, 単独のヘテロ原子とは大きく異なる反応性を示す。しかし, この興味深い化学的現象は, これまで精密有機合成への応用は見過ごされてきた。アミド基の窒素原子に対し, 反応性制御素子としてアルコキシ基を導入した「多置換アミンの3段階迅速合成法」を確立した。1段階目は「アミドとアルデヒドのカップリング反応」, 2段階目は「アミドカルボニル基への求核付加反応」, 3段階目は「求電子的アミノ化反応」である。いずれの段階もN-メトキシ基による反応性制御が必須であった。また, 用いる有機金属試薬の自由な組み合わせにより, 天然物ファシクラリンを含む多様な含窒素化合物の迅速供給が可能になった。
We developed a three-step synthesis of multi-substituted amines from N-alkoxyamides. Utilization of the N-alkoxy group as a reactivity control element was the key to success in this three-step synthesis. The first reaction was the N-alkoxyamide/aldehyde coupling reaction. The N-alkoxy group of amides enhanced the nucleophilicity of the nitrogen, enabling the direct coupling reaction. The second reaction was nucleophilic addition to the N-alkoxyamides. Incorporation of the N-alkoxy group into the amides increased the electrophilicity of the amide carbonyls and promoted the chelation effect. The third reaction was electrophilic amination using the resulting N-alkoxyamines. The developed method was applicable to a variety of substrates, resulting in the elaboration of multi-substituted amines including complex alkaloids such as fasicularin.
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研究種目 : 基盤研究(C)(一般)
研究期間 : 2015~2017
課題番号 : 15K05436
研究分野 : 有機化学
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