アルデヒドの銅で触媒化された非対称プロパルギレーション
Daniel R Fandrick1, Keith R Fandrick, Jonathan T Reeves
1Chemical Development, Boehringer Ingelheim Pharmaceuticals Inc., 900 Ridgebury Road/P.O. Box 368, Ridgefield, Connecticut 06877-0368, USA. daniel.fandrick@boehringer-ingelheim.com
Journal of the American Chemical Society
|May 21, 2010
まとめ
銅触媒は,プロパルギルボロラン試料を使用してアルデヒドの非対称プロパルギレーションを可能にします. この方法は,様々なアルデヒドに対する高い選択性を達成し,さらなる合成のための貴重なキラル中間物質を作成します.
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
- アシンメトリック・シンセシス
背景:
- アルデヒドの機能化は,有機合成において極めて重要です.
- キラルの構成要素を作るためのエナンチオセレクティブ・メソッドの開発は,重要な課題です.
研究 の 目的:
- アルデヒドの銅触媒による新しい非対称プロパルギレーションを報告する.
- プロパルギルボロランの反応剤を用いて,高いエナチオセレクティブ性と地域セレクティブ性を用いる.
主な方法:
- アルデヒドとプロパルギルボロランの反応剤との銅触媒反応.
- 様々なアルデヒド基板を用いたエナンチオ選択性および地域選択性の分析.
- 機能グループ耐性の実証.
主要な成果:
- 高度にエナチオと地域選択性の高い銅触媒による非対称プロパルギレーションを達成した.
- アリファティック,ビニル,およびアリルアルデヒドの間で観察された幅広い機能群の耐性.
- 多種多様な基板に対して高いエナンチオ選択性を得られた.
結論:
- 開発された方法論は,キラルホモプロパルギルアルコールへの効率的な経路を提供します.
- その結果得られたTMSホモプロパルギルアルコールは,簡単にキラル型ジヒドロピラノンに変換される,多用途の中間物質です.
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