サルフォニウムイリドから生成されたキラルオルガンボランの合成と応用

Varinder K Aggarwal¹, Guang Yu Fang, Andreas T Schmidt

¹School of Chemistry, University of Bristol, Cantock's Close, Bristol BS8 1TS, U.K. v.aggarwal@bristol.ac.uk

Journal of the American Chemical Society

|February 11, 2005

まとめ

アリル安定硫黄イリドは,ボランと反応して,クリーンなモノホモロゲーションをします. キラル硫化物を用いた非対称反応は,高いエナチオセレクティブ性を出し,抗炎症薬の合成を可能にします.

科学分野:

有機化学オーガニック・ケミストリー
アシンメトリック・シンセシス

背景:

スルフォニウムイリドは,有機合成における多用途の反応剤である.
ボランは,多様な用途を持つ重要な有機金属化合物です.

研究の目的:

アリル安定化スルフォニウムイリドとトライキル/トリアリルボランの反応を調査する.
ボランの非対称的同型化方法を開発する.
開発した方法を医薬品化合物の合成に適用する.

主な方法:

アリル安定化スルフォニウムイリドが様々なトライキル/トライアリルボランと反応する.
ホモロゲーション製品のアルコールとアミンの分離.
非対称性を誘発するためにキラル硫化物の使用.
キラルクロマトグラフィを用いたエナンチオ選択性の分析.

主要な成果:

ボランのクリーンモノホモロゲーションは,最小限の高いホモロゲーション製品 (<10%) で達成されました.
反応は低温 (5°Cから-78°C) で効率的に進行した.
非対称反応では一貫して高いエナンチオセレクティブ性 (>95% ee) が観察されました.

結論:

イライド-ボラン反応は,ボランの同型化のための簡単で効率的な経路を提供します.
開発された非対称的な方法は,高度にエナチオセレクティブであり,複雑な分子合成に適用できます.
この反応は,抗炎症剤のネボノジンとセチリジンの合成に成功しました.

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