触媒エナチオセレクティブのニトロソ・ディエルス-アルダー反応

Biplab Maji¹, Hisashi Yamamoto¹

¹Molecular Catalyst Research Center, Chubu University , 1200 Matsumoto-cho, Kasugai, Aichi 487-8501, Japan.

Journal of the American Chemical Society

|November 27, 2015

まとめ

この研究は,新しい銅触媒による非対称なニトロゾ・ディエルス・アルダー反応を導入する. この方法は薬剤発見に役立つ高い選択性を持つ複雑な有機分子を効率的に合成します

科学分野:

有機化学
非対称な触媒
合成方法論

背景:

ニトロゾ・ディエルス・アルダー反応 (NDA) は,ヘテロサイクルの化合物を合成するための貴重なツールである.
NDA反応の非対称的な変種を開発することは,エナティオメリクルの純粋な分子にアクセスするために不可欠です.

研究の目的:

Cu ((I)) -DTBM-セグフォスを誘導した非対称な分子間NDA反応を開発する.
高ステレオ制御で3,6-ジヒドロ-1,2-オクサジンおよび関連派生物を合成する.

主な方法:

Cu ((I)) -DTBM-セグフォスの触媒システムを使用した.
ピリミジンおよびピリダジン誘導体から派生した反応性ニトロゾ化合物.
異なった形で置換された周期的1,3-ダイエンと反応した.

主要な成果:

サイクロードパイプでは高収率 (最大99%) を達成した.
優れた地域選択性 (> 99:1) とエナチオ選択性 (> 99% ee) を示した.
コンドゥラミンA-1とナルシクラシンを正式に合成する方法を成功裏に応用した.

結論:

発展した触媒システムは複雑なキラル分子への効率的な経路を提供する.
この方法論は,非対称なNDA反応の範囲を拡大します.
自然製品合成のための貴重な中間材料にアクセスできます.

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