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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
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サルフォキシミンの有機触媒運動解像度
Shunxi Dong1, Marcus Frings1, Hanchao Cheng1
1Institute of Organic Chemistry, RWTH Aachen University , Landoltweg 1, 52074 Aachen, Germany.
Journal of the American Chemical Society
|February 6, 2016
まとめ
チラルのN-ヘテロサイクリックカルベンの触媒は,エナルを用いて硫素ヒミンの効率的な動的分解を可能にします. この方法は,高純度で両方のエナチオマーを提供し,製薬用途のためのグラムスケールの合成を容易にします.
科学分野:
- 有機化学
- キャタリシス
- 非対称合成
背景:
- サルフォキシミンは有機合成における重要なキラル構成要素である.
- 薬剤開発には,それらのエナチオセレクティブ合成のための効率的な方法の開発が不可欠です.
研究 の 目的:
- サルフォキシミンの運動分解のための新しい触媒システムを開発する.
- アミダーション反応において高いエナチオ選択性を達成する.
- 有価な化合物を合成する方法のスケーラビリティと有用性を実証する.
主な方法:
- エナルを用いた硫素ヒミンの運動解像度.
- キラルなN-ヘテロサイクリックカルベン (NHC) 触媒を使用する.
- ステレオセレクティブ・アミデーション アシル移転剤なし
主要な成果:
- 優れたエナティオメア過剰 (ee) 値 (最大99% eeと-97% ee) を有する硫黄素の効率的な運動解像度を達成した.
- sulfoximinesの両方のエナントオマーを取得する能力を実証しました.
- 反応をグラムスケールで成功させた.
- FXa阻害剤の非対称合成で回収されたスルフォキシミンを利用した.
結論:
- チラルのNHC触媒によるセルフォキシミンとエナルの運動分解は,非常に効率的でステレオ選択的な方法である.
- このプロトコルは,硫黄素素の高純度エナントイオマーの両方へのアクセスを提供します.
- 薬剤中間物質の合成におけるスケーラビリティと応用は,この方法論の実用的な重要性を強調しています.
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