Catalytic Desymmetrizing Carbonyl–Amine Condensation Reaction to Construct Axially Chiral Diaryl Ethers

IF 4.7 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2026-10-16 Epub Date: 2026-10-01 DOI:10.1021/acs.orglett.6c03721

Tao Huang, Ze-Xin Zhou, Hui-Ling Zhou, Xu-Ping Liu, Yan-Fei Niu, Yi-Yuan Peng, Qiu-Ping Ding, Xing-Ping Zeng

引用次数: 0

Abstract

Catalytic desymmetrizing carbonyl–amine condensation (CAC) reactions between prochiral 2,6-diamino diaryl ethers and cyclobutane-1,3-diones have been developed for the highly enantioselective synthesis of axially chiral diaryl ethers in up to 99% ee values. This reaction represents the first application of prochiral aromatic amines in catalytically asymmetric CAC reactions. Control experiments revealed that cyclobutane-1,3-diones showed an obviously higher reactivity and enantioselectivities in these asymmetric CAC reactions.

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催化脱对称羰基-胺缩合反应制备轴手性二芳醚

摘要：采用催化脱对称羰基胺缩合反应（CAC），在2,6-二氨基二芳醚和环丁烷-1,3-二酮之间合成了具有高度对映选择性的轴手性二芳醚，其ee值高达99%。该反应是前手性芳香胺在催化不对称CAC反应中的首次应用。对照实验表明，环丁烷-1,3-二酮在这些不对称CAC反应中表现出明显较高的反应活性和对映选择性。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.