A kinetic resolution accompanied chirality transformation process for asymmetric synthesis of chiral phenol, oxaziridine, and α-hydroxyl cyclic ketone

IF 10.4 1区化学 Q1 CHEMISTRY, MULTIDISCIPLINARY

Science China Chemistry Pub Date : 2024-08-08 DOI:10.1007/s11426-024-2038-5

Pengxin Wang, Xiaoyong Zhang, Lingqing Wang, Rui Wang, Dongxu Yang

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引用次数: 0

Abstract

Chirality transformation is a basic, attractive, and important strategy for obtaining enantioenriched products with desired chiral elements. The reported chirality conversion reaction often involves the process from one type of chirality to another one. To better utilize the chirality transformation strategy for obtaining two or more products with different chiral elements in a single reaction, a new method of kinetic resolution accompanied by a chirality transformation protocol is proposed and successfully realized in this study. This process is used for the asymmetric oxidation of phenol compounds along with the kinetic resolution of oxaziridines. A wide scope of products, including axially chiral phenols, oxaziridines, and α-hydroxyl cyclic ketones were smoothly obtained in high levels of yields and enantioselectivities in the developed method. These products can be readily used for the synthesis of various types of chiral ligands, which are potential choices for other catalytic asymmetric reactions.

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手性苯酚、恶嗪脒和α-羟基环酮不对称合成的动力学解析伴随手性转化过程

手性转化是获得具有所需手性元素的对映体富集产物的一种基本、有吸引力的重要策略。所报道的手性转化反应通常涉及从一种手性到另一种手性的过程。为了更好地利用手性转化策略在单一反应中获得两种或多种具有不同手性元素的产物，本研究提出了一种新的动力学解析方法，并成功实现了手性转化方案。该工艺用于苯酚化合物的不对称氧化以及恶嗪类化合物的动力学解析。在所开发的方法中，包括轴向手性苯酚、草吖啶和 α-羟基环酮在内的多种产品都以高产率和高对映选择性顺利获得。这些产物可用于合成各种类型的手性配体，是其他催化不对称反应的潜在选择。

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

Science China Chemistry CHEMISTRY, MULTIDISCIPLINARY-

CiteScore

14.40

自引率

7.30%

发文量

3787

审稿时长

2.2 months

期刊介绍： Science China Chemistry, co-sponsored by the Chinese Academy of Sciences and the National Natural Science Foundation of China and published by Science China Press, publishes high-quality original research in both basic and applied chemistry. Indexed by Science Citation Index, it is a premier academic journal in the field. Categories of articles include: Highlights. Brief summaries and scholarly comments on recent research achievements in any field of chemistry. Perspectives. Concise reports on thelatest chemistry trends of interest to scientists worldwide, including discussions of research breakthroughs and interpretations of important science and funding policies. Reviews. In-depth summaries of representative results and achievements of the past 5–10 years in selected topics based on or closely related to the research expertise of the authors, providing a thorough assessment of the significance, current status, and future research directions of the field.