Atroposelective Desymmetrizing Iodination via Chiral Phosphoric Acid Catalysis: Synthesis of Axially Chiral Biaryl Phosphine Oxides

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.6c03558

Yan Chang, Yushen Gao, Xinghua Wang, An-An Zhang, Mingliang Zhang, Gaowei Li, Bing-Bing Song, Yuan-Yuan Gao, Qiuling Song, Lantao Liu

引用次数: 0

Abstract

Herein, we report a CPA-catalyzed atroposelective iodination of prochiral phosphine oxides bearing no hydrogen-bond-donor substituents, affording a range of 3′-iodinated axially chiral biaryl phosphine oxides in excellent yields and enantioselectivities. The reaction proceeds through synergistic noncovalent interactions among the iodinating reagent, the catalyst, and the substrate, eliminating the need for substrate pre-functionalization or external additives. The method accommodates both di-tert-butyl and dicyclohexyl phosphine oxide substrates, as well as diverse substitution patterns on both aromatic rings.

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手性磷酸催化下的氨选择性去对称碘化：轴向手性联芳基膦氧化物的合成

摘要本文报道了一种不含氢键供体取代基的前手性膦氧化物的羧基选择性碘化反应，得到了一系列具有优异产率和对映选择性的3′-碘化轴手性联芳基膦氧化物。该反应通过碘化试剂、催化剂和底物之间的协同非共价相互作用进行，不需要底物预功能化或外部添加剂。该方法可容纳二叔丁基和双环己基氧化膦底物，以及两种芳香环上的不同取代图案。

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.