アルケンの触媒的な二酸化ステレオおよびエナチオ選択的フッ素アミネーション
Katrina M Mennie1, Steven M Banik1, Elaine C Reichert1
1Department of Chemistry & Chemical Biology , Harvard University , Cambridge , Massachusetts 02138 , United States.
Journal of the American Chemical Society
|March 28, 2018
まとめ
この研究では,触媒を用いたキラル・フッ素化ビルディングブロックを合成する新しい方法が報告されています. このアプローチは,薬剤発見のための価値あるフッ素有機化合物への高度な選択的なアクセスを提供します.
科学分野:
- 有機化学
- 非対称合成
- 化化学
背景:
- チラルのフッ素有機化合物は,医薬品化学における重要な構成要素です.
- 合成のための効率的でステレオ選択的な方法の開発は,依然として大きな課題です.
研究 の 目的:
- syn-β-fluoroaziridine誘導体のステレオ選択的合成のための新しい触媒システムを開発する.
- 複数のステレオセンターを持つ他のフッ素化合物へのアクセスのためのこの方法の有用性を調査する.
主な方法:
- HF-ピリジンとmCPBAを用いたアリルアミンのキラルアリルヨウ素触媒による化.
- 複合フッ素アミンの合成のために,触媒制御されたダイアステレオ選択性を利用する.
- 開発された方法を様々なアルケンの基板に適用する.
主要な成果:
- シン-β-フッ素アジリジンの合成における高ダイアステレオ選択性およびエナチオ選択性.
- 連続した3つのステレオセンターを持つ1,3-difluoro-2-aminesのエンアンチオ濃縮の成功.
- 様々な基板から抗β-フッ素ピロリジンと1,2-オキシフッ素化製品へのアクセス
結論:
- 開発されたキラルアリルヨウ素触媒は,有価なフッ素有機基の効率的なステレオ選択合成を可能にします.
- この方法は,複数のステレオセンターを持つ複雑なフッ素分子にアクセスするための広範な適用性を提供します.
- この研究は,フッ素化医薬品と農薬の合成のための強力なツールを提供します.
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