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钴催化手性二芳基甲胺的对映选择性 C-H 烷氧基化反应合成。

Synthesis of Chiral Diarylmethylamines by Cobalt-Catalyzed Enantioselective C-H Alkoxylation.

机构信息

Center of Chemistry for Frontier Technologies, Department of Chemistry, Zhejiang University, Hangzhou, 310027, China.

School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, 453007, China.

出版信息

Angew Chem Int Ed Engl. 2023 Jul 10;62(28):e202304706. doi: 10.1002/anie.202304706. Epub 2023 Jun 5.

Abstract

Chiral diarylmethylamines (DAMA) are important structural motifs widely present in pharmaceuticals, natural products, and chiral ligands. Herein, we reported a highly enantioselective synthesis of chiral DAMAs via cobalt-catalyzed enantioselective C-H alkoxylation strategy. The reaction features easy operation, the use of earth-abundant and cost-efficient cobalt(II) catalyst, and readily available ligand. A range of chiral DAMAs were efficiently synthesized in high yields with excellent enantioselectivities (up to 90 % yield and up to 99 % ee) through desymmetrization and parallel kinetic resolution. Moreover, this protocol was also compatible with the synthesis of chiral benzylamines via kinetic resolution.

摘要

手性二芳基甲胺(DAMA)是广泛存在于药物、天然产物和手性配体中的重要结构基序。在此,我们报道了一种通过钴催化的对映选择性 C-H 烷氧基化策略高效合成手性 DAMAs 的方法。该反应具有操作简单、使用丰富且廉价的钴(II)催化剂以及易得配体的特点。通过去对称化和并行动力学拆分,高效合成了一系列手性 DAMAs,产率高,对映选择性好(最高可达 90%的产率和 99%的 ee)。此外,该方法还适用于通过动力学拆分合成手性苄胺。

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