Au(PPh3)Cl/AgOTf/TsOH 催化的 1-(2-羟基苯基)丙炔醇和 β-氧酮类（酰胺，酸）的级联反应：顺式-3a,8a-二氢呋喃并[2,3-b]苯并呋喃框架的非对映选择性构建

IF 3.6 2区化学 Q1 CHEMISTRY, ORGANIC

Journal of Organic Chemistry Pub Date : 2024-11-20 DOI:10.1021/acs.joc.4c02430

Yangyi Zhang, Guisheng Deng

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引用次数: 0

摘要

在 Au(PPh3)Cl/AgOTf/TsOH/MeCN/N2/25 °C体系中，以 1-(2-羟基苯基)-3-芳基丙-2-炔-1-醇和β-氧代酮类（酰胺、酸）为起始原料，实现了在 8a 位上具有取代基的顺式-3a,8a-二氢呋喃并[2,3-b]苯并呋喃衍生物的非对映选择性合成。研究表明，底物中亚甲基的酸性在差异反应中起着关键作用。亚甲基的酸性越强，越有利于实现理想的转化。TsOH 作为添加酸在合成策略中的独特作用也得到了合理的解释。2-氧代膦酸盐、2-氧代磺酸盐和 3-氧代丁酸盐适合用于转化。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Au(PPh3)Cl/AgOTf/TsOH-Catalyzed Cascade Reaction between 1-(2-Hydroxyphenyl)-propargyl Alcohols and β-Oxoketones (Amides, Acid): Diastereoselective Construction of cis-3a,8a-Dihydrofuro[2,3-b]benzofuran Framework

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In the Au(PPh₃)Cl/AgOTf/TsOH/MeCN/N₂/25 °C system, diastereoselective synthesis of cis-3a,8a-dihydrofuro[2,3-b]benzofuran derivatives with a substituent at the 8a-position has been achieved by using 1-(2-hydroxyphenyl)-3-arylprop-2-yn-1-ols and β-oxoketones (amides, acid) as starting materials. The studies revealed that the acidity of methylene in substrates plays a key role in the differential reactions. A stronger acidity of the methylene is favorable in the desired conversion. The unique role of TsOH as an additive acid in the synthesis strategy has been rationalized. 2-Oxo-phosphonate, 2-oxo-sulfonate, and 3-oxobutanoate are suitable for the conversion.

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来源期刊

Journal of Organic Chemistry 化学-有机化学

CiteScore

6.20

自引率

11.10%

发文量

1467

审稿时长

2 months

期刊介绍： Journal of Organic Chemistry welcomes original contributions of fundamental research in all branches of the theory and practice of organic chemistry. In selecting manuscripts for publication, the editors place emphasis on the quality and novelty of the work, as well as the breadth of interest to the organic chemistry community.