炭素,窒素,酸素核愛者とアルレンの分子内外水素機能化のための高活性Au (I) 触媒である
Zhibin Zhang1, Cong Liu, Robert E Kinder
1P. M. Gross Chemical Laboratory, Duke University, Durham, North Carolina 27708-0346, USA.
Journal of the American Chemical Society
|July 13, 2006
まとめ
金で触媒化された反応は,アルネイル化合物から窒素と酸素のヘテロサイクルを効率的に形成します. この方法により,高収量と選択性が得られ,複雑なサイクルにおいてキラリティの移転さえ行われます.
科学分野:
- 有機化学 オーガニック・ケミストリー
- カタリシス カタリシス カタリシス
- 合成方法論 合成方法論
背景:
- 金の触媒は,有機合成の強力なツールとして登場しました.
- 内分子反応は,循環性化合物への効率的な経路を提供します.
研究 の 目的:
- アレニル基板の分子内ヒドロアミナ化およびヒドロアルコキシル化におけるゴールド (I) 触媒の有用性を調査する.
- N-アレニルカルバメート,アレニルアルコール,および2アレニルインドールを含むAu (I) -触媒化されたサイクライゼーションの範囲と限界を調査する.
主な方法:
- Au[P(t-Bu) 2(o-ビフェニル) ]ClとAgOTfをダイオキサンで触媒システムを使用しました.
- N-アレニルカルバメートの分子内ヒドロアミネーションを研究した.
- ガンマ-およびデルタ-ヒドロキシアルレンの分子内ヒドロアルコシライゼーションを調べました.
- 2-アレニルインドールの分子内水酸化を研究した.
主要な成果:
- 内部分子ヒドロアミネーションによるビニルピロリジン誘導体の合成で95%の収量を達成しました.
- N-アレニルカルバメトからピペリジン誘導体の効率的な形成が実証されています.
- ハイドロキシアレンから酸素ヘテロサイクルの形成において,良好な収量と高いエクソ選択性が報告されています.
- 2-アレニルインドールから合成された4-ビニルテトラヒドロカルバゾールが良好な収量.
- キラルアレンリル部分のサイクル化において,新しく形成されたステレオジェニックセンターへの軸性キラル性の移転を観察した.
結論:
- 金 ((I) カタリシスは,様々なアルネル化合物の分子内水素酸化,水素アルコキシル化,および水素アリル化に非常に効果的です.
- 開発された方法論は,ピロリジン,ピペリジン,テトラヒドロカルバゾールを含む多様なヘテロサイクルのスキャファードにアクセスできます.
- 反応は多様な機能群を許容し,キラリティの移転によるエナチオセレクティブサイクリングを含む優れたステレオ化学的制御を示します.
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