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フェノールとプロパルギル炭酸から2 - アリロキシ-1,3 - ディエンの合成

Naoki Ishida¹, Yusaku Hori¹, Shintaro Okumura¹

¹Department of Synthetic Chemistry and Biological Chemistry , Kyoto University , Katsura, Kyoto 615-8510 , Japan.

Journal of the American Chemical Society

|December 20, 2018

まとめ

新しいニッケル触媒反応は,プロパルギル炭酸とフェノールからステレオ選択的に有価な2-アリオキシ-1,3-ダイエンを効率的に合成します. この方法は,幅広い機能群の許容性を提供し,ダイエルス-アルダー反応を含む様々な合成用途に有用なダイエンを生成します.

科学分野:

有機化学
カタリシス
合成方法論

背景:

1,3-ディエンは有機合成の重要な構成要素である.
1,3-ダイエンを合成するための既存の方法は,効率が低く,広く適用できない可能性があります.
機能化されたダイーンへのステレオ選択的経路の開発は非常に望ましい.

研究の目的:

2-アリオキシ-1,3-ダイエンの合成のための新しく便利な方法について報告する.
簡単に入手できる材料を用いてステレオ選択的合成を行う.
合成されたダイエンの有用性をさらに化学的変換で示すために.

主な方法:

プロパルギル炭酸とフェノール間のニッケル触媒結合反応.
高いステレオ選択性を達成するために反応条件の最適化.
合成された2 - アリオキシ - 1,3 - ディエンの特徴と機能群の耐性の評価.

主要な成果:

2-リオキシ-1,3-ディエンの成功し,ステレオ選択的合成.
ヨド,ホルミール,ボリルを含む幅広い機能群の耐性が観察された.
合成されたダイエンは,その後の反応のための貴重な中間物質である.

結論:

便利でステレオ選択的なニッケル触媒による2−アリオキシ−1,3−ダイエンの合成方法が開発された.
この方法は優れた機能的グループ耐性を示し,合成の有用性を拡大しています.
結果の1,3-ダイエンは,特にディエルス-アルダー反応では,多用途のシントンである.

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