非活性化された1,1-代替アルケンの銅触媒によるエナンチオセレクティブ水酸化
Won Jun Jang1, Seung Min Song1, Jong Hun Moon1
1Department of Chemistry and Institute of Basic Science, Sungkyunkwan University , Suwon 16419, Korea.
Journal of the American Chemical Society
|September 14, 2017
まとめ
この研究は,アルケンのエナチオセレクティブ水酸化のための効率的な触媒法を導入する. このプロセスは,高い選択性と機能群耐性を有するエナティオメール濃縮された製品を生成します.
科学分野:
- 有機化学
- カタリシス
- 非対称合成
背景:
- ハイドロボレーションは有機合成の重要な反応です
- 1,1-非置換アルケンのような基質に挑戦するエナンチオセレクティブの方法の開発は重要な目標です.
研究 の 目的:
- アリファティック1,1-非置換アルケンの効率的で高度なエナチオセレクティブの水酸化を開発する.
- エナティオメリックに濃縮されたβ-キラルアルキルピナコルボロナートを簡単に作る.
主な方法:
- ホスフィン・コッパー触媒を用いて水酸化反応を行った.
- ボロンの源としてピナコルボランを使用した.
- 1,1-代替アルケンの範囲を調査した.
主要な成果:
- ハイドロボレーションでは99%まで高いエナンチオセレクティビティが得られる.
- ゲミナルアルキル置換剤の間の前例のないエナチオディスクリミネーションが観察されました.
- 1mol %の触媒負荷で機能群の互換性と効率性を証明した.
- グラムスケールの合成が成功しました.
結論:
- 開発されたフォスフィン-Cu触媒化水酸化は,エナチオメリックに濃縮されたβ-キラルアルキルピナコルボロナートを合成するための効率的な方法である.
- この方法は,さまざまな1,1-非置換アルケンの優れた選択性と広範な適用性を示しています.
- 低触媒負荷とグラムスケールの可行性は,この変換の実用性を強調しています.
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