アキラルアリル炭酸塩のレジオおよびエナチオセレクティブ・イリジウム触媒型分子間アリルエーテル化により,フェノキシドを用いたアキラルアリルエーテル化

Fernando López¹, Toshimichi Ohmura, John F Hartwig

¹Department of Chemistry, Yale University, P.O. Box 208107, New Haven, Connecticut 06520-8107, USA.

Journal of the American Chemical Society

|March 20, 2003

まとめ

この研究は,イリジウム触媒反応を導入し,高い選択性を持つキラルアリルアルリルエーテルを形成します. この方法は,単純な前駆体から貴重な化合物を効率的に合成し,非対称合成を進める.

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・カタリシス
有機金属化学有機金属化学

背景:

アリルエーテル化は,複雑な有機分子を合成するために極めて重要です.
エナチオセレクティブとレジオセレクティブの方法の開発は,有機合成における重要な課題です.

研究の目的:

イリジウム触媒による新種のエナチオセレクティブおよびレジオセレクティブのアリルエーテル化を開発する.
高い収穫量と選択性を持つキラルアリルエーテルを合成する.

主な方法:

イリジウム・フォスフォラミドイト複合体を触媒として利用した.
アキラル型アリル型電極性を持つナトリウムおよびリチウムアリロキシドを使用しています.
最適な結果を得るために,テトラヒドロフラン (THF) の反応を調査した.

主要な成果:

キラルアリルエーテル合成において,高収量と優れた地域およびエナチオ選択性を達成した.
様々な置換されたおよびステリカルに阻害されたアリロキシドに対する耐性が実証されています.
アルキル (E) - アリル炭酸から派生した製品では,高いエナティオメール過量 (ee) が観察されています.

結論:

開発されたイリジウム触媒方式は,キラルアリルエーテルへの効率的な経路を提供します.
この反応は,広範囲の基質範囲と高いステレオ化学的制御を提供します.
この研究は,非対称な触媒と有機合成の分野に大きく貢献しています.

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