非対称な有機触媒的モノフルオロビニレーション
Christian Borch Jacobsen1, Martin Nielsen, Dennis Worgull
1Center for Catalysis, Department of Chemistry, Aarhus University, Langelandsgade 140, DK-8000 Aarhus C, Denmark.
Journal of the American Chemical Society
|April 26, 2011
まとめ
器官触媒的モノフルオロビニレーション反応は,α-fluoro-β-keto-benzothiazolesulfonesを用いて開発されました. この方法により,エナンチオ濃縮モノフッ素ビニル化製品およびバイサイクル化合物に選択的にアクセスできます.
科学分野:
- 有機化学 オーガニック・ケミストリー
- カタリシス カタリシス カタリシス
- フロアンの化学的性質
背景:
- オーガノカタリシスは非対称な合成を可能にします.
- フッ素化合物は,医薬品と材料科学において重要である.
- 選択的なフルオロビニレーションの方法の開発は困難です.
研究 の 目的:
- 高度にエナチオおよびダイアステロセレクティブの有機触媒的モノフルオロビニレーション反応を開発する.
- 各種の電ophilesにモノフルオロビニルアニオンシントンの正式な添加を実証する.
- 複合的なフッ素化分子の合成を調査する.
主な方法:
- α-フッ素β-ケトβ-ベンゾチアゾールスルフォンが主要反応剤として用いられる.
- モノフルオロビニレーションの有機触媒条件.
- アサイクリック・エノン,サイクリック・エノン,イミンとの反応.
主要な成果:
- モノフッ素ビニル化製品のE-およびZ-同体の両方の選択的合成.
- 純粋なダイアステレオアイソマーの分離は,良好から優れた収量 (最大99% ee) を得ることができます.
- モノフルオロビニル基を含む,高度にエナンチオ濃縮されたバイサイクル化合物の形成.
結論:
- 開発された方法論は,非対称的なモノフルオロビニレーションのための強力なツールを提供します.
- このアプローチにより,複雑なフッ素有機分子を作製することができます.
- E:Z-選択性のメカニズム的根拠が提供されました.
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