Chiral Phosphoric Acid-Catalyzed Asymmetric Synthesis of Axially Chiral Arylpyrazole

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC Organic Letters Pub Date : 2025-01-23 DOI:10.1021/acs.orglett.4c03996

Shujun Tong, Jiaqi Pu, Yu Qi, Shi-Wu Li

引用次数: 0

Abstract

A chiral phosphoric acid-catalyzed efficient, operationally simple, general method for straightforward syntheses of axially chiral arylpyrazole employing N-alkyl of 3-aryl-5-aminopyrazoles reacting with azonaphthalenes was achieved. A wide variety of axially chiral heterobiaryl diamines in generally good yields with excellent enantioselectivities were obtained under mild conditions. In addition, a scaled-up experiment and postmodification of the chiral product further highlighted the synthetic utility.

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手性磷酸催化不对称合成轴手性芳基吡唑

采用手性磷酸催化3-芳基-5-氨基吡唑n -烷基与偶氮萘反应，获得了一种高效、操作简单、通用的轴手性芳基吡唑合成方法。在温和的条件下，得到了种类繁多的轴手性杂二胺，收率普遍较高，对映选择性好。此外，手性产物的放大实验和后修饰进一步突出了其合成实用性。

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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.