Grignardの反応剤によるZ-Selective銅触媒による非対称性アリルアルキル化
Massimo Giannerini1, Martín Fañanás-Mastral, Ben L Feringa
1Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG Groningen, The Netherlands.
Journal of the American Chemical Society
|February 23, 2012
まとめ
銅の触媒は,グリニャード反応剤を用いて,アリル石二塩化からキラルZ-ビニル塩化物の選択的合成を可能にします. これらの多用途な化合物は,クロスカップリング反応を通じて光学的に活性なZアルケンとダイエンを生成するための重要な中間物質です.
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
- 合成方法論 合成方法論
背景:
- アリルアルキレーションは,有機合成における基本的な変換である.
- 複雑な分子を作るためのエナチオセレクティブ・メソッドの開発は,依然として重要な課題です.
- ビニル塩化物は,有機合成における貴重な構成要素である.
研究 の 目的:
- エナチオセレクティブアリルアルキレーションのための新しい銅触媒法を開発する.
- 簡単に入手可能なアリル性ジェム-ジクロライドからキラルZ-ビニルクロライドを合成する.
- 合成されたビニル塩化物の有用性を,その後の変換で実証する.
主な方法:
- 銅で触媒化されたアリル性アルキル化によるアリル性ジェム・ジクロライドのグリニャード反応剤によるアルキル化.
- キラルリガンドを用いたエナンチオセレクティブ合成.
- スズキのクロスカップリング反応は,さらなる機能化のために.
主要な成果:
- アリルアルキル化において,高い地域およびエナチオ選択性 (ERは99:1まで) を達成した.
- 一連のキラルZ-ビニル塩化物の合成に成功しました.
- これらのシントンの変換をスズキカップリングで光学的に活性なZ-アルケーンと1,3-cis,トランスダイーンに示した.
結論:
- 開発された銅触媒法により,価値あるキラルZ-ビニルクロライド合成に効率的にアクセスできます.
- この方法論は,エナチオメリックに濃縮されたアルケンとダイエンのための多用途な経路を提供します.
- この研究は,非対称合成におけるアリル性宝石二塩化物の合成的有用性を拡大する.
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