アリルアルコールの触媒的レジオおよびエナチオ選択的ハロアジデーション
Frederick J Seidl1, Chang Min1, Jovan A Lopez1
1Department of Chemistry , Stanford University , Stanford , California 94305 , United States.
Journal of the American Chemical Society
|November 8, 2018
まとめ
この研究により,アリルアルコールの新しいエナンチオセレクティブハロアジデーション反応が導入され,単純な出発材料から貴重なキラル構成要素が生成される. この方法は,ブロムまたは塩素を効率的に組み込み,新しい結合ダイエン反応を含む広範な適用性を実証しています.
科学分野:
- 有機化学
- 非対称合成
- 合成方法論
背景:
- アリルアルコールは多用途の合成中間物質である.
- アルケンの機能化のためのエナチオ選択的方法の開発は,有機合成において極めて重要です.
- ハロアジデーション反応は,さまざまな窒素およびハロゲンを含む化合物への経路を提供します.
研究 の 目的:
- アリルアルコールの高地域性およびステレオ選択性エナチオ選択性ハロアジデーションを開発する.
- ブロミンや塩素を電化ハロゲン源として組み込むことを研究する.
- チラルの構成要素として得られた製品の有用性を実証し,アザ糖を合成する方法論を適用する.
主な方法:
- 簡単に入手可能な材料を用いたアリルアルコールのエナンチオセレクティブハロアジデーション.
- 様々なアルキル置換アルケンの反応最適化.
- ハリド群とアジド群のステレオ特異的変換
- 結合ダイエンのエナチオ選択的1,4-ハロアジデーションへの方法の適用.
主要な成果:
- アリルアルコールの高度に地域選択的およびステレオ選択的エナチオ選択的ハロアジデーションが達成されました.
- この反応でブロムと塩素の両方が成功しました.
- 製品のハライドとアジド群はステレオ特異的に価値ある構成要素に変換された.
- 結合ダイエンの最初のエナンチオセレクティブ1,4-ハロアジデーションが報告されました.
結論:
- この新しいハロアジデーション反応は,エナティオメリックに濃縮されたハロおよびアジド機能化された化合物への効率的な経路を提供します.
- この方法論は,アザ糖を含む複雑な分子を合成するための汎用的なプラットフォームを提供します.
- 後の変換のステレオ特異性は,合成中間物質としての製品の有用性を高めます.
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