エナチオセレクティブ (形式) アザ・ディエルス・アルダー反応は,ダニシェフスキー型以外のダイエネを用いて行われます

Uttam K Tambar¹, Sharon K Lee, James L Leighton

¹Department of Chemistry, Columbia University, New York, New York 10027, USA.

Journal of the American Chemical Society

|July 29, 2010

まとめ

チラルシリコンのルイス酸は,エナチオセレクティブなアザ-ディエルス-アルダー反応を触媒化する. この効率的な方法は,温和な条件下で,高いエナチオ選択性を持つ多様なテトラヒドロピリジンを合成します.

科学分野:

有機化学オーガニック・ケミストリー
アシンメトリック・シンセシス

背景:

aza-Diels-Alder反応は,窒素を含むヘテロサイクルを構成するための強力なツールです.
生物学的活性を持つキラル分子にアクセスするために,エナンチオセレクティブの変異種を開発することは極めて重要です.

研究の目的:

新規のエナチオセレクティブ形式のアザ-ディエルス-アルダー反応を開発する.
単純で経済的なキラルシリコンのルイス酸を触媒として利用する.
多種多様なテトラヒドロピリジン誘導体を合成する.

主な方法:

反応パートナーとしてアシルヒドラゾン (グリオキシラートとアリファートアルデヒドから派生) を採用する.
非ダニシェフスキー型ダイエンを反応に利用する.
環境温度条件下で,キラルシリコンのルイス酸による触媒.

主要な成果:

formal aza-Diels-Alder反応のエナンチオセレクティブの開発に成功しました.
幅広い基板範囲で,様々なヒドラゾーンとダイーンに対応します.
優れたエナチオセレクティビティを持つ多様なテトラヒドロピリジンの合成.

結論:

開発された方法は,エナチオメリックに濃縮されたテトラヒドロピリジンへの効率的かつ経済的経路を提供します.
キラルシリコンのルイス酸は,これらの変換を促進するのに有効です.
このアプローチは,さらなる合成アプリケーションのための貴重なキラル構成要素へのアクセスを提供します.

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