ステレオ特異のクロスカップリングにおけるナフチル要件を克服して四次ステレオセンターを形成する
Jianyu Xu1, Olivia P Bercher1, Mary P Watson1
1Department of Chemistry & Biochemistry, University of Delaware, Newark, Delaware 19716, United States.
Journal of the American Chemical Society
|June 1, 2021
まとめ
新しいスズキ-ミヤウラクロスカップリング方法は,三次ベンジルカルボキシラートのステレオ特異的合成のために単純なスティルベネリガンドを使用する. この突破は,複雑なダイアリル四極性ステレオセンターを作るための"ナフチル要件"を克服しました.
科学分野:
- 有機化学
- カタリシス
- ステレオ選択合成
背景:
- ステレオ特異的なクロスカップリングは 複雑な分子合成に不可欠です
- 既存の方法では,ナプチル群のような特定の置換素が,エナチオ濃縮された電ophiles に必要である.
- "ナフチル要求"は,ステレオスペシフィッククロスカップリング反応の範囲を制限する.
研究 の 目的:
- スズキ-ミヤウラクロスカップリングの新技術開発
- ナフチル置換剤を欠いた三次ベンジル炭酸塩の合成を可能にします.
- 現在のステレオスペシフィック・クロスカップリングの限界を克服する.
主な方法:
- スズキ-ミヤウラ交互結合反応で単純なスティルベネリガンドを使用した.
- ナフチル基を持たないものを含め,基板として使用された三次ベンジルカルボキシラート.
- 新しい炭素-炭素結合の形成においてステレオ特異性を達成することに焦点を当てています.
主要な成果:
- 三次ベンジルカルボキシレートのステレオスペシフィックなスズキ-ミヤウラクロスカップリングが成功しました.
- 挑戦的な全炭素ダイアリル四分型ステレオセンターの設置を実証した.
- 良質の産物で,エナティオメール過量 (ee) が高い.
結論:
- 開発された方法は,ナフチル置換剤の必要性を排除することによって,画期的な進歩をもたらします.
- このアプローチは,複雑な分子構造を構築するためのステレオスペシフィッククロスカップリングの有用性を拡大します.
- 非対称合成と触媒の 重要な進歩です
![Solid-phase Synthesis of [4.4] Spirocyclic Oximes](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F58508.jpg&w=3840&q=50)
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