アルケンのアミノアリレーションのための二機能反応剤としてのアリルスルフォニラセタミド
Timothy M Monos1, Rory C McAtee1, Corey R J Stephenson2
1Department of Chemistry, University of Michigan, Ann Arbor, MI, USA.
Science (New York, N.Y.)
|September 29, 2018
まとめ
新しい触媒法により,アルケンのアミノアリレーションにより2,2-ダイアリエチアミンの合成が可能である. この可視光による反応は効率的で 選択的で 簡単に手に入る材料を使います
科学分野:
- 有機化学
- 合成化学
- カタリシス
背景:
- アルケンのアミノアリレーションは有機合成における重要な変換である.
- 簡潔で効率的なC-Nボンドの構築方法の開発は極めて重要です.
- 既存の方法は多くのステップや 厳しい条件を必要とします
研究 の 目的:
- アルケンのアミノアリレーションのための新しい触媒プロトコルを開発する.
- アリル硫ニラセタミドをアルケーンに添加することで,アンチ・マルコヴニコフ・地域選択性および高いダイアステロ選択性を達成する.
- 2,2-ダイアリエチラミンの合成のための可視光駆動の,リドックス中性反応を確立する.
主な方法:
- 電子豊富なアルケーンにアリルスルフォニラセタミドを触媒的に添加する.
- 単一の二機能反応剤を用いてC−N結合を形成する.
- 単電子アルケンの酸化を可能にするために可視光光還元触媒を使用します.
主要な成果:
- 完全な反マルコヴニコフ型地域選択性が達成された.
- 優れたダイアステレオ選択性が認められ,2,2-ダイアリエチラミンを生成した.
- 反応は室温で進み,二酸化硫黄と幅広い機能群の互換性が失われます.
結論:
- 開発されたプロトコルは2,2-ダイアリエチラミンの簡潔で効率的な合成戦略を提供します.
- 反応メカニズムは,重要なベンジル基の中間物質がスマイルス- トゥース 1, 5 アリルシフトを経験することを含む.
- この可視光媒介プロセスは,温和な条件と容易に入手可能な材料により,多様な合成用途に適しています.
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