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通过 N-杂环卡宾催化的半亚胺的对映选择性动态动力学拆分。

Atroposelective Dynamic Kinetic Resolution via Hemiaminals Catalyzed by N-Heterocyclic Carbene.

机构信息

School of Pharmaceutical Sciences, Key Laboratory of Bioorganic Phosphorous Chemistry & Chemical Biology (Ministry of Education), Tsinghua University, Beijing 100084, P. R. China.

出版信息

Org Lett. 2021 Oct 15;23(20):7765-7770. doi: 10.1021/acs.orglett.1c02780. Epub 2021 Sep 27.

Abstract

Axially chiral amino acids and its derivatives are vital building blocks of bioactive molecules, artificial peptides, and asymmetric catalysts. Herein, we report an unprecedented carbene-catalyzed atroposelective dynamic kinetic resolution to access axially chiral amino esters via hemiaminals. This protocol features a broad substrate scope and good functional group tolerance and allows the rapid assembly of axially chiral amino esters in good to high yields with high enantioselectivities.

摘要

手性轴氨基酸及其衍生物是生物活性分子、人工肽和不对称催化剂的重要构建模块。在此,我们报告了一种前所未有的卡宾催化的动态动力学拆分反应,通过半亚胺来获得手性轴氨基酸酯。该方案具有广泛的底物范围和良好的官能团耐受性,能够以良好到高的收率和高对映选择性快速构建手性轴氨基酸酯。

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