アミノcyclopropanesのダイナミック運動非対称 [3 + 2] キャンセル反応
Florian de Nanteuil1, Eloisa Serrano, Daniele Perrotta
1Laboratory of Catalysis and Organic Synthesis, Ecole Polytechnique Fédérale de Lausanne, EPFL SB ISIC LCSO , BCH 4306, 1015 Lausanne, Switzerland.
Journal of the American Chemical Society
|April 16, 2014
まとめ
研究者は,銅触媒を用いた新しいダイナミック・キネティック・アシンメトリック・アヌレーション反応を開発した. この方法は,アミノcyclopropanes,エノールエーテル,およびアルデヒドから,有効なエナンチオ濃縮された窒素化合物を効率的に合成します.
科学分野:
- 有機化学 オーガニック・ケミストリー
- アシンメトリック・シンセシス
- カタリシス カタリシス カタリシス
背景:
- 窒素を含むヘテロサイクルは,医薬品化学における重要な支架である.
- それらの合成のための効率的でエナチオセレクティブな方法の開発は,重要な課題です.
研究 の 目的:
- アミノcyclopropanes.の最初の動的運動非対称 [3 + 2] キャンセル反応を報告する.
- エナチオ濃縮窒素の構成要素にアクセスするための汎用的な方法を提供すること.
主な方法:
- 商業的に利用可能なビソクサゾリンのリガンドと組み合わせた銅の触媒を使用しました.
- 採用されたアミノcyclopropanesは,最適化された条件下でエノールエーテルとアルデヒドと反応します.
主要な成果:
- サイクロペンチルおよびテトラヒドロフューリラミンについて,高収量 (69-99%) を達成した.
- 優れたエナチオセレクティブ性を得,エナチオメア比率は最大98:2.
- 単一の条件下で反応の有効性を実証した.
結論:
- 開発された方法は,エナンチオ濃縮窒素ヘテロサイクルの強力な新しい経路を提供します.
- このアプローチは,複雑な生物活性分子の合成を容易にする.
- 銅触媒による非対称無効反応の有用性を強調する.
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