アルケンの保護されていない2-アジドアミンの直接合成
Szabolcs Makai1, Eric Falk1, Bill Morandi1
1ETH Zürich, Vladimir-Prelog-Weg 3, HCI, 8093 Zürich, Switzerland.
Journal of the American Chemical Society
|December 10, 2020
まとめ
アルケーンから2アジドアミンを合成する 簡単な鉄触媒の方法を開発しました これらの化合物は,生物学的活性分子と薬剤発見において重要な近隣ダイアミンの前駆体です.
科学分野:
- 有機化学
- 合成化学
- キャタリシス
背景:
- 付近のダイアミンは,多くの生物学的活性化合物や医薬品で一般的な構造モチーフです.
- 主要な2-アジドアミンは,近隣のダイアミンへのアクセスのための貴重な合成前駆体として機能する.
- これらの前駆物質を合成するための効率的で汎用的な方法の開発は,医薬品化学と医薬品開発にとって極めて重要です.
研究 の 目的:
- 無防備な原発2アジドアミンの 新しく単純な合成を報告する
- この目的のためにアルケンの機能不全における鉄触媒の有用性を実証する.
- 開発された方法論の広範な適用性と機能群の許容性を示します.
主な方法:
- 様々なアルケンの基質の鉄触媒による機能低下.
- 保護されていないプライマリ2-アジドアミンを主要な中間物質として利用する.
- その後,アジドアミン群の化学選択派生.
主要な成果:
- 薬剤のような複雑な分子と三ペプチドを含む様々なアルケンの原始的2アジドアミンの合成に成功した.
- アジドアミン群の容易な誘導性を示し,その隠されたダイアミン性質を強調した.
- RO 20-1724の合成と (±) -ハマカンチンBと (±) -キナゴリドの正式な全合成にこの方法論を適用した.
結論:
- 開発された鉄触媒反応は,2-アジドアミンへの効率的で高度な機能群耐性経路を提供する.
- この方法は,近隣のダイアミンとその誘導体にアクセスするための多用途のプラットフォームを提供します.
- 合成アプリケーションは,複雑な分子合成におけるこの方法の幅広い可能性を強調しています.
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