アリルアジドのダイナミック・キネティック解像度
Amy A Ott1, Charles S Goshey1, Joseph J Topczewski1
1Department of Chemistry, University of Minnesota Twin Cities , Minneapolis, Minnesota 55455, United States.
Journal of the American Chemical Society
|June 3, 2017
まとめ
この研究は,アリルアジドの動的運動解像度を用いて複雑なアミンを生成する新しい方法を導入している. このアプローチは,キラルな窒素化合物の合成を簡素化し,高いエナチオ選択性を達成します.
科学分野:
- 有機化学
- アシンメトリック・シンセシス
背景:
- 合成化学における重要な課題は,エナティオメリックに純粋な機能化されたアミンを製造することである.
- 既存の方法はしばしば複雑なアミン構造を作り出すのに苦労するか,難しい結合形成を必要とします.
研究 の 目的:
- 密度の高い機能化されたアミンのエナチオセレクティブ合成のための新しい触媒的方法を開発する.
- ダイナミック・キネティック解像度でのラセミゼーション経路としてウィンシュタイン再配置を利用する.
主な方法:
- アルケンの機能化のためにシャープレス二酸化反応を用いて,三次アジドを生成する.
- ダイナミックな動的解像度戦略を 実行する. ウィンシュタインの再編成を含む.
主要な成果:
- 卓越したエナチオ選択性 (最大99:1er) を獲得し,三次アジドを形成する.
- ステレオセンターで直接のC-NまたはC-C結合形成なしに,三次アジドセンターでキラリティを成功裏に確立した.
- 更に合成処理可能な追加機能の導入を証明した.
結論:
- ウィンシュタイン再配列は,エナチオセレクティブアミン合成の動的運動解像度で効果的に使用できます.
- この方法は,多様な機能を持つキラル三次アジドへの汎用的な経路を提供します.
- この戦略は,複雑なキラルアミンの構築を簡素化し,幅広い合成用途を提供します.
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