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マイケル反応は,軸性キラルビアリルのアトロポセレクティブ構築を促した
Shengyi Yan1, Wang Xia1, Shaoyu Li1,2
1Shenzhen Grubbs Institute and Department of Chemistry, Guangdong Key Laboratory of Catalysis, Southern University of Science and Technology, Shenzhen 518055, China.
Journal of the American Chemical Society
|April 9, 2020
まとめ
新しい銅触媒反応は,新しいリガンドを使用して,アゾナフタレンとアリルボロン酸からキラルビアリル化合物を生成する. この方法は,光学的に活性なビアリルおよび関連する機能分子を合成するための効率的で穏やかな代替手段を提供します.
科学分野:
- 有機化学
- 非対称な触媒
- 合成方法論
背景:
- 軸性バイアリルは,医薬品と材料科学における重要な構造モチーフである.
- ビアリルアトロピソマーを合成するための既存の方法は,しばしば厳しい条件またはステキオキシダントを必要とします.
- キラルビアリルの構築のための効率的で選択的な触媒的方法の開発は,依然として重要な課題です.
研究 の 目的:
- ビアリルアトロピソマーを合成するための最初の銅触媒によるアトロポセレクティブ マイケル型添加物を確立する.
- 添加反応における高いエナチオ選択性を促進するための新しいキラルリガンドを開発する.
- 合成されたアトロピソメアの有用性を,さらなる機能化によって実証する.
主な方法:
- アゾナフタレンとアリルボロン酸の間の,銅触媒によるミカエル型添加反応.
- キラルリガンドとして新しいBINOL由来フォスフォラミド酸を使用した.
- アリル-アリル結合形成を促進し,副反応を抑制する反応条件の最適化.
主要な成果:
- 良い効率と高い選択性で,幅広いアトロピソメアビアリルを成功裏に合成した.
- 新しい触媒システムは,アリル-アリルキラル軸の形成を効果的に促進しました.
- 軸性キラルリガンド,触媒,機能性アトロピソマーへの変換を通じてアプローチの汎用性を実証した.
- 通常のC−H結合方法に伴う酸化物質と厳しい条件の必要性を回避した.
結論:
- ビアリルアトロピソメアのアトロポセレクティブ合成のための新しく効率的な銅触媒法を確立した.
- 開発された方法論は,光学的に活性なビアリルへのアクセスのための既存の経路に直接的で穏やかな代替手段を提供します.
- 合成されたキラルビアリルは,触媒と材料科学における多様な応用のための貴重な前駆体として機能する.
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