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钯接力催化实现炔烃的不对称双羟羰基化反应生成手性琥珀酸。

Asymmetric Double Hydroxycarbonylation of Alkynes to Chiral Succinic Acids Enabled by Palladium Relay Catalysis.

机构信息

Shanghai Frontiers Science Center of Molecule Intelligent Syntheses, Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai, 200062, P. R. China.

Institute of Molecular Science, Key Laboratory of Materials for Energy Conversion and Storage of Shanxi Province, Shanxi University, Taiyuan, 030006, P. R. China.

出版信息

Angew Chem Int Ed Engl. 2022 Jul 18;61(29):e202204156. doi: 10.1002/anie.202204156. Epub 2022 May 20.

Abstract

A Pd-catalyzed asymmetric double hydroxycarbonylation of terminal alkynes was developed by using relay catalysis, providing a highly efficient route to chiral succinic acids (41 examples, 76-94 %, 94-99 % ee). Key to success was the combinatorial use of a Pd precursor with two distinct phosphine ligands in one pot. The synthetic utilities of this protocol were showcased in the facile synthesis of key intermediates for chiral pharmaceuticals.

摘要

钯催化的末端炔烃不对称双羟羰基化反应是通过接力催化发展起来的,为手性琥珀酸的合成提供了一条高效的途径(41 个实例,76-94%,94-99%ee)。成功的关键是在一锅反应中组合使用两种不同膦配体的钯前体。该方法的合成实用性在手性药物关键中间体的简便合成中得到了展示。

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