二機能アミノ反応剤を用いたステレオ特異アルケンのアジリディネーション: アザ・プリレザエフ反応
Joshua J Farndon1, Tom A Young1, John F Bower1
1School of Chemistry , University of Bristol , Bristol BS8 1TS , United Kingdom.
Journal of the American Chemical Society
|December 14, 2018
まとめ
O-T活性化N-Bocヒドロキシラミンのトリフロアセチン酸 (TFA) 脱保護は,分子内アジリジネーションを誘導する. この反応は,分子間応用の可能性のあるステレオ特異なメカニズムを通じて,複雑なN-ヘテロサイクルリングを効率的に形成します.
科学分野:
- 有機化学
- 合成化学
- ヘテロサイクル化学
背景:
- N-Bocヒドロキシラミンは多用途の合成中間物質である.
- 水酸化素の活性化が,その後の反応に不可欠である.
- 複雑な構造への効率的な経路を提供する.
研究 の 目的:
- O-Tが活性化したN-Bocヒドロキシラミンの in situ 脱保護を調査する.
- 分子内アジリディネーションによるN-ヘテロサイクルのリングシステムの形成を調査する.
- 反応メカニズムを解明し,分子間可行性を評価する.
主な方法:
- トリフッ素酸 (TFA) を使ってインシット・デプロテクション
- O-T活性化されたN-BocヒドロキシラミンとN-テテッドアルケンの合成.
- 反応機構とステレオ化学を決定するための合成と計算研究.
主要な成果:
- N系アルケンの分子内アジリディネーションの成功
- 複雑なN-ヘテロサイクルリングの形成.
- アザ・プリレザエフ型のダイアステレオ特異的メカニズムを確認
結論:
- インサイト脱保護は,分子内アジリディネーションへの簡単な経路を提供します.
- この反応は高度にステレオセレクティブで,複雑なヘテロサイクルの構造を生み出します.
- この方法論は,関連する分子間アジリディネーション反応に希望を示しています.
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