1,2-アザボリンに対するボロン保護グループ戦略
Andrew W Baggett1, Shih-Yuan Liu1
1Department of Chemistry, Boston College , Chestnut Hill, Massachusetts 02467-3860, United States.
Journal of the American Chemical Society
|October 3, 2017
まとめ
研究者は1,2-アザボリンからアルキル群とアリル群を除去する新しい方法を開発し,保護群として使用することが可能になった. この画期的な発見により,生物医学および医薬品化学に関連する新しいBN同位体の合成が可能になりました.
科学分野:
- 有機化学
- 薬剤化学
- 合成化学
背景:
- 1,2-アザボリンは多用途のヘテロサイクル化合物である.
- 1,2-アザボリンのB-アルコキシド分子は容易に変化し,特定の反応での使用を制限する.
- アルキル基とアリル基は,以前は,ボロン位置の除去可能な保護基として機能しなかった.
研究 の 目的:
- 1,2-アザボリンのボロンの位置を簡単に除去する方法を開発する.
- アルキル基とアリル基を除去可能なボールの保護基として使用できるようにする.
- バイオメディカルと医薬品の用途のための新しいBNイソステル合成.
主な方法:
- 1,2-アザボリンと分子酸素またはディートルブチルペロキシドの反応.
- 銅の塩とアルコールを触媒として使用する.
- N-デプロトン化1,2-アザボリンを用いてエポキシードリングを開く.
主要な成果:
- B-アルキルまたはB-アリル分子を1,2-アザボリンでB-アルコキシド断片に交換した.
- アルキル基とアリル基を,ボールの有効な除去可能な保護基として示す.
- 以前に入手不可能だったエチルベンゼンのBNイソステルの合成.
- ディヒドロベンゾフランとベンゾフランのBN同位体へのアクセス
結論:
- 1,2-アザボリンにおけるボロン除去のための新しい効率的な方法が確立されています.
- この方法論は,有機合成における1,2-アザボリンの合成有用性を拡大する.
- 開発されたアプローチは,薬剤発見と天然製品合成のための価値あるBNイソステルの作成を容易にする.
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