ダブルオルガノフォテロドックスと銅の触媒によって可能になった非対称プロパルギル基のシアネーション
Fu-Dong Lu1, Dan Liu1, Lei Zhu2
1CCNU-uOttawa Joint Research Centre, Key Laboratory of Pesticide and Chemical Biology, Ministry of Education, College of Chemistry , Central China Normal University , 152 Luoyu Road , Wuhan 430079 , China.
Journal of the American Chemical Society
|April 2, 2019
まとめ
この研究は,二重光還元と銅の触媒を用いた最初の非対称プロパルギル基シアネーションを導入する. この方法は,高いエナチオ選択性を持つ光学的に活性なプロパルギルシアン化物を効率的に生成します.
科学分野:
- 有機化学
- カタリシス
- 非対称合成
背景:
- プロパルギルシアン酸は 有価な合成中間物質です
- プロパルギル基の非対称なシアネーションは依然として困難です.
研究 の 目的:
- プロパルギル基のシアネーションのための最初のエナンチオセレクティブ法を開発する.
- 光学的に活性なプロパルギルサイアニドの合成において,高い収量とエナチオ選択性を達成する.
主な方法:
- 有機光触媒とキラル銅複合体を採用した二重触媒.
- フォトレドックス触媒によるプロパルギル基の生成
- キラル銅触媒によって媒介されるエナンチオセレクティブシアネーション.
主要な成果:
- 多種多様な光学的に活性なプロパルギルサイアニドの合成に成功した.
- 高い反応率 (57~97%) とエナチオ選択性 (83~98% ee) を達成した.
- 反応の広範な適用性を28例で示した.
結論:
- 開発された二重触媒システムは,非対称プロパルギル基のシアネーションに非常に有効です.
- 反応経路と立体化学的制御に関する洞察をメカニズム研究から得ることができる.
- この研究は,価値あるキラルプロパルギルシアン化物への新しい経路を提供します.
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