ダイアゾ化合物のエナチオセレクティブ・コパー・カタライズド・オキシアルキニレーション
Durga Prasad Hari1, Jerome Waser1
1Laboratory of Catalysis and Organic Synthesis, Ecole Polytechnique Fédérale de Lausanne, EPFL SB ISIC LCSO , BCH 4306, 1015 Lausanne, Switzerland.
Journal of the American Chemical Society
|June 17, 2017
まとめ
この研究は,ダイアゾ化合物から価値あるキラル構成要素を合成するための新しいエナチオ選択的触媒方法を導入しています. 銅で触媒化されたオキシアルキニレーションは,エナチオピュアα-ベンゾイロキシプロパルギルエステルへの効率的なアクセスを提供します.
科学分野:
- 有機化学
- カタリシス
- 合成化学
背景:
- エナチオセレクティブ合成は,キラルの構成要素にアクセスするために不可欠です.
- ディアゾ化合物は有機合成における多用途の前駆体である.
- ダイアゾ化合物への核性および電性粒子の同時添加は,効率的な合成経路を提供します.
研究 の 目的:
- ダイアゾ化合物のオキシアルキニル化のための高度なエナチオ選択的触媒方法の開発.
- この変換のためにエチニルベンジオドコソロン反応剤を使用します.
- エナチオピュア α-ベンゾイロキシプロパリルエステルへのアクセスを提供する.
主な方法:
- 単純な銅ビソクサゾリン触媒を用いる.
- エチニルベンジオドコソロン反応剤と反応するダイアゾ化合物
- 添加反応で高いエナチオ選択性を達成する.
主要な成果:
- 高い反純度を持つα-ベンゾイロキシプロパルギルエステルの合成に成功した.
- これらのエステルが構成要素としての有用性を示した.
- エナチオピュリティの損失なしに,製品をヴィシンアル二酸化物とα-ヒドロキシプロパルギルエステルに効率的に変換する.
結論:
- 開発された方法は,価値あるキラル中間物質への簡単でエナチオセレクティブな経路を提供します.
- ダイアゾ化合物の銅触媒酸化は強力な合成戦略である.
- 結果として得られる製品は,さらなる化学的変換のための多機能な前駆体として機能します.
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