Rh触媒による非対称水素化による高効率のエナンチオセレクティブ合成
Qiaozhi Yan1, Guiying Xiao1, Ying Wang1
1Key Laboratory of Radiopharmaceuticals, College of Chemistry , Beijing Normal University , Beijing 100875 , China.
Journal of the American Chemical Society
|January 8, 2019
まとめ
新しいRh- ((R,R) -f-スピロフォスは,不飽和な前駆体からキラル・スルフォンを効率的に生成します. この方法は,薬剤の中間物質を含む様々な基板に対して高いエナチオ選択性を達成します.
科学分野:
- 有機化学
- 非対称な触媒
背景:
- サルフォンは,医薬品と材料科学で応用できる多用途有機化合物です.
- 生物学的活性分子へのアクセスには,キラルサルフォン合成のためのエナンチオセレクティブの方法の開発が不可欠です.
研究 の 目的:
- 非飽和スルフォンの非対称な水素化のための高効率でエナントオセレクティブな触媒システムを開発する.
- 開発された様々な硫黄基板の触媒システムの範囲と限界を調査する.
主な方法:
- 触媒としてRh-R,R-f-spiroPhos複合体を利用した.
- 軽い条件下で非対称な水素化反応を行った.
- 3,3-ダイアリル,エクソサイクル α,β-不飽和スルフォン,3-アルキル-3-アリルスルフォン,およびベンゾ[b]チオフェン-1,1-二酸化物の水素化を調査した.
主要な成果:
- 様々な不飽和スルフォンの不対称な水素化のために,高いエナチオ選択性 (最大99. 9% ee) を達成した.
- 基質のステリック障害,電子特性,幾何学に関係なく,触媒の有効性を実証した.
- (S) - ((+)) - アールターメロンへの経路を含む,キラルスルフォンを成功的に合成した.
結論:
- Rh- ((R,R) -f-spiroPhosの触媒化水素化は,優れたエナチオ選択性を持つキラルスルフォン合成のための強力な方法である.
- この方法論は,医薬品合成のための価値あるキラルの構成要素へのアクセスを提供します.
- 反応の広範囲の基質と温和な条件は,それを実用的な合成ツールにします.
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