Enantioselective synthesis of 10-allylanthrones via iridium-catalyzed allylic substitution reaction

A highly enantioselective allylic substitution reaction of anthrones with aromatic or aliphatic allyl carbonates was realized by using iridium catalyst prepared from [Ir(COD)Cl]2 and BHPphos. Substituted 10-allylanthrones were obtained in excellent yields and with excellent enantioselectivity and regioselectivity (up to 98% yield, 99% ee) under mild conditions.

Graphical abstractIridium-catalyzed asymmetric intermolecular Friedel–Crafts type allylic substitution reaction of anthrones was developed, affording C10 substituted allylanthrones in good to excellent yields, regioselectivity and enantioselectivity.Figure optionsDownload full-size imageDownload as PowerPoint slide