Palladium-Monodentate Phosphoramidite Catalysisによって可能になったアルケンの非対称なマルコヴニコフ製ヒドロアミノカルボニレーション

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Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions

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Published on: March 20, 2014

Ya-Hong Yao¹, Hui-Yi Yang¹, Ming Chen¹

¹Key Laboratory of Synthetic and Nature Molecule of Ministry of Education, Department of Chemistry & Materials Science, Northwest University, Xi'an 710127, P.R. China.

Journal of the American Chemical Society

|December 29, 2020

まとめ

2-置換プロパナミドを合成する新しい方法は,不対称なマルコヴニコフ製水素アミノカルボニレーションのためのパラジウム触媒を用いる. この効率的なプロセスはシンプルな材料から価値あるキラル分子を作り出します

科学分野:

有機化学
カタリシス
非対称合成

背景:

キラルアミドの合成は,医薬品化学と材料科学において極めて重要です.
アミド合成のための原子経済学とエナチオ選択的方法の開発は,依然として重要な課題である.

研究の目的:

アルケンのアニリンによるマルコフニコフ型非対称パラジウム触媒化水酸化化合物の開発.
α-ステレオセンターで2代入プロパナミドの原子経済的な合成を達成する.

主な方法:

パラジウム触媒で新しいフォスフォラミジットリガンド (L16) を利用した.
入手可能なアルケンとアニリンを原料として使用した.
周囲の条件下で反応を行った.

主要な成果:

高度反応性で選択的なマルコフニコフ型水素アミノカーボニレーションを達成した.
合成された2置換プロパナミドは,高い地域およびエナチオ選択性を持つα-ステレオセンターを有する.
幅広い機能群に対する耐性を示した.

結論:

開発された方法は,キラル-2-置換プロパナミドへの簡単で直接的な経路を提供します.
反応は,メカニズムの研究によって支持されたパラジウム水素経路を経由します.
このアプローチは,エナチオメリックに濃縮されたアミドにアクセスするための貴重なツールを提供します.

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