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

IF 1.5 4区化学 Q3 CHEMISTRY, ORGANIC

Tetrahedron Letters Pub Date : 2024-09-25 DOI:10.1016/j.tetlet.2024.155311

引用次数: 0

Abstract

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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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

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。

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来源期刊

Tetrahedron Letters 化学-有机化学

CiteScore

3.50

自引率

5.60%

发文量

521

审稿时长

28 days

期刊介绍： Tetrahedron Letters provides maximum dissemination of outstanding developments in organic chemistry. The journal is published weekly and covers developments in techniques, structures, methods and conclusions in experimental and theoretical organic chemistry. Rapid publication of timely and significant research results enables researchers from all over the world to transmit quickly their new contributions to large, international audiences.