カタリティック・アシンメトリック・リバース・ヒドロボレーションによるステレオダイバーゲント合成
Tao-Tao Gao1, Wen-Wen Zhang1, Xin Sun1
1Center of Basic Molecular Science, Department of Chemistry , Tsinghua University , Beijing , 100084 , China.
Journal of the American Chemical Society
|February 27, 2019
まとめ
研究者は有機合成のための高選択性Rh触媒化水酸化方法を開発した. この新しいアプローチはステレオ化学を正確に制御し,薬剤発見と天然製品合成のための複雑なキラル分子の効率的な合成を可能にします.
科学分野:
- 有機合成
- カタリシス
- ステレオ化学
背景:
- 化学的,地域的,ダイアステレオ的,およびエナチオ選択性の制御は有機合成において極めて重要です.
- 一つの分子のすべてのステレオアイソマーの合成は,薬剤発見のための天然製品アナログ合成とキラル化合物ライブラリ作成を支援します.
- マルチステレオセンター合成における相対的および絶対的構成の精密な制御は,非対称な触媒では依然として課題である.
研究 の 目的:
- 新しい触媒制御の水酸化反応を 開発する
- 複数のステレオセンターを持つ分子の合成で前例のない選択性を達成する.
- キラルの構成要素のステレオダイバージェント合成のための多用途な戦略を提供する.
主な方法:
- ピナコルボランを用いたα,β不飽和カルボニル化合物のRh触媒化水酸化.
- ステレオ化学的結果を制御するために,基板幾何学 (EまたはZ) とリガンドエナティオマー (SまたはR) を利用する.
- ボールを含む製品のステレオ特異的変換.
主要な成果:
- 水酸化反応は,高い地域性,ダイアステレオ性,およびエナチオ選択性で進行した.
- 2つの近隣のステレオセンターは,水浸し製品で成功裏に生成されました.
- すべての可能なダイアステレオイソメルは,基板とリガンドをチューニングすることによって容易に入手可能であった.
- ボロンを含む製品は,ステレオ特異的な反応によって,様々なキラル構成要素に変換された.
結論:
- 高度に選択的な触媒制御された水溶解が開発された.
- この方法は複数のステレオセンターを正確に制御し,非対称合成の重要な課題に取り組んでいます.
- この戦略により,有価なキラル化合物の効率的かつステレオダイバージェントな合成が可能になる.
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