一种奎宁方酰胺催化的对映体选择性[4 + 2]环加成反应，用于制备手性 3, 4-二氢香豆素的邻羟基苯基对苯醌甲醚和γ-丁烯酸酯

IF 16.4 1区化学 Q1 CHEMISTRY, MULTIDISCIPLINARY

Accounts of Chemical Research Pub Date : 2024-09-25 DOI:10.1016/j.tetlet.2024.155311

Jing-Liang Yu , Su-Fan Gao , Chun-Jun Zhu , Wen-Sheng Li , Li-Xin Wang

引用次数: 0

摘要

本研究揭示了在γ-丁烯内酯和邻羟基苯基对-QMs 之间发生的一种奎宁-夸父酰胺催化的对映体选择性逆电子需求异狄尔斯-阿尔德反应。在温和的条件下，直接简洁地制备了多种具有两个相邻立体中心的手性 3、4-二氢香豆素框架，并取得了极佳的效果（收率高达 94%，dr 为 99:1，er 为 98:2）。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

A quinine squaramide catalyzed enantioselective [4 + 2] cycloaddition between ortho-hydroxyphenyl para-quinone methide and γ-butenolides for preparation of chiral 3, 4-dihydrocoumarins

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A quinine squaramide catalyzed enantioselective [4 + 2] cycloaddition between ortho-hydroxyphenyl para-quinone methide and γ-butenolides for preparation of chiral 3, 4-dihydrocoumarins

A quinine-squaramide catalyzed enantioselective inverse-electron-demand hetero-Diels–Alder reaction between γ-butenolides and ortho-hydroxyphenyl p-QMs has been disclosed. A wide range of chiral 3, 4-dihydrocoumarins frameworks with two adjacent stereogenic centers have been directly and concisely prepared in excellent results (up to 94 % yield, 99:1 dr, 98:2 er) under mild conditions.

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来源期刊

Accounts of Chemical Research 化学-化学综合

CiteScore

31.40

自引率

1.10%

发文量

312

审稿时长

2 months

期刊介绍： Accounts of Chemical Research presents short, concise and critical articles offering easy-to-read overviews of basic research and applications in all areas of chemistry and biochemistry. These short reviews focus on research from the author’s own laboratory and are designed to teach the reader about a research project. In addition, Accounts of Chemical Research publishes commentaries that give an informed opinion on a current research problem. Special Issues online are devoted to a single topic of unusual activity and significance. Accounts of Chemical Research replaces the traditional article abstract with an article "Conspectus." These entries synopsize the research affording the reader a closer look at the content and significance of an article. Through this provision of a more detailed description of the article contents, the Conspectus enhances the article's discoverability by search engines and the exposure for the research.