Guangdong Provincial Key Laboratory of Chiral Molecule and Drug Discovery, School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou 510006, China.
Org Lett. 2020 Apr 17;22(8):2925-2930. doi: 10.1021/acs.orglett.0c00587. Epub 2020 Apr 1.
An enantioselective cyclization of diazoindolinones with -hydroxymethyl chalcones has been established by a cooperative dirhodium complex and chiral phosphonic acid catalysis under mild conditions. This reaction is the first example of catalytic asymmetric intramolecular Michael-type trapping of oxonium ylide enabled by phosphoric acid through a dual H-bonding activation model, which provides an efficient access to the chiral spirochroman-3,3-oxindoles, with vicinal quaternary and tertiary stereocenters, in good to excellent yields and enantioselectivities.
通过双铑配合物和手性磷酸协同催化，在温和条件下实现了重氮吲哚啉酮与β-羟甲基查耳酮的对映选择性环化反应。该反应是首例通过双氢键活化模式实现的手性磷酸催化的氧鎓叶立德的不对称分子内迈克尔加成反应，为构建具有相邻季碳和三级手性中心的手性螺色满-3,3-吲哚啉提供了有效的方法，具有良好到优秀的收率和对映选择性。
