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簡単に利用可能なキラルアルデヒドとしてRh触媒アルキン水酸化のためのα-アミノアルデヒド

Joel F Hooper¹, Sangwon Seo¹, Fiona R Truscott¹

¹Department of Chemistry, Chemistry Research Laboratory, University of Oxford , Mansfield Road, Oxford, OX1 3TA, U.K.

Journal of the American Chemical Society

|January 16, 2016

まとめ

Rh触媒によるアルキン水酸化反応は,メチルチオメチル (MTM) 保護基を持つα-アミノアルデヒドを効率的に利用する. この方法は,温和な条件,広範囲の基板,そして貴重なアミノエノンの合成のための高いステレオ特異性を提供します.

科学分野:

有機化学
カタリシス
合成方法論

背景:

α-アミノアルデヒドは有機合成における多用途な構成要素である.
複合分子における反応性を制御するためにグループ戦略の保護が不可欠です
ロジウム触媒反応は炭素-炭素結合形成のための強力なツールを提供します.

研究の目的:

α-アミノアルデヒドの効率的なRh触媒化水酸化を開発する.
この新しい合成方法の範囲と限界を探求する.
自然製品の合成で得られる製品の有用性を実証する.

主な方法:

窒素結合メチルチオメチル (MTM) 保護基を備えた容易に入手可能なα-アミノアルデヒドを使用する.
軽度の条件下でRh触媒によるアルキン水酸化を用いる.
小口角ビスフォスフィンリガンドを使用し,反応性と選択性を高めます.

主要な成果:

様々なアミノ酸とフェニルラクティック酸から派生したものを含む様々なα-アミノアルデヒドの水酸化を成功させた.
優れた機能的グループ耐性と高いステレオ特異性を示した.
合成されたα-アミノエノンの製品で,さらなる変換の可能性があります.

結論:

開発されたRh触媒による水酸化は,α-アミノエノンの合成のための効率的な方法である.
MTM保護グループは,軽度でステレオ特異な条件下で反応を容易にします.
合成の有用性は,スフィンゴシンの短いエナチオセレクティブ合成によって強調されています.

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