チラル・ビノールベースのアルコキシードによるアリルアルコールの運動解像度:実験と理論の研究の組み合わせ
Yidong Liu, Song Liu, Dongmei Li
1Department of Chemistry , Sungkyunkwan University , 2066, Seobu-ro , Jangan-gu, Suwon , Gyeonggi 440-746 , Korea.
Journal of the American Chemical Society
|December 19, 2018
まとめ
この研究は,BINOL由来触媒を用いたキラル二次アリルアルコールを生成するための新しい移行金属のない方法を導入しています. このエナチオセレクティブ・イソメリゼーションは,天然製品の合成における応用により,高い収穫量と選択性を提供します.
科学分野:
- 有機化学
- 非対称な触媒
背景:
- チラルの二次アリルアルコールは有価な合成中間物質である.
- 既存の方法はしばしば移行金属に依存するか,高いエナチオ選択性がない.
研究 の 目的:
- アリルアルコールのエナンチオセレクティブ,移行金属フリーな触媒的運動解像度を開発する.
- キラル二次アリルアルコールを合成するために,高いエナティオメア過剰 (ee) と選択性.
主な方法:
- キラルビノール誘導体ベースのアルコキシドの合成
- バイ機能的なブロンステッド塩基触媒によって触媒化された非対称性イソメリゼーション
- 活性種と反応経路を特定するためのメカニズム研究
主要な成果:
- BINOLから派生した有望なキラルブレンステッド塩基触媒を特定した.
- 高いエナチオ選択性 (最大99%) と選択性 (S因数 > 200) を得ている.
- 天然産物 (+) ヴェラゲンシンを合成する効果を示した.
結論:
- この研究は,キラル二次アリルアルコールを合成するための最初の移行金属無塩基触媒化異体化に成功しました.
- BINOLのフェノールグループは,水素結合によって反応性およびエナチオ選択性において重要な役割を果たします.
- 開発された戦略は,複雑な生物活性分子の合成に適用できます.
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