低负荷方酰胺在水中催化3,4 -二氢吡喃酮的对映选择性合成

IF 4 2区化学 Q2 CHEMISTRY, APPLIED

Advanced Synthesis & Catalysis Pub Date : 2025-10-07 DOI:10.1002/adsc.70141

Tianxing Li, Xinxin Li, Jinfeng Zhang, Hui Jin, Lixin Zhang

引用次数: 0

摘要

β -酮硫酯和β，γ -不饱和α -酮酯在0.2 mol%脯氨酸衍生的方酰胺的催化下，在室温下4小时内以74-98%的收率和90-99%的ee生成3,4 -二氢吡喃酮。结合核磁共振和计算研究表征了产物的酮-烯醇互变异构行为，而合成应用包括具有全碳季立体中心的3,4 -二氢吡喃酮的非对映选择性构建。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Enantioselective Synthesis of 3,4‐Dihydropyranones via Low‐Loading Squaramide Catalysis “on Water”

查看原文本刊更多论文

Enantioselective Synthesis of 3,4‐Dihydropyranones via Low‐Loading Squaramide Catalysis “on Water”

An organocatalytic “on‐water” cascade reaction of β‐ketothioesters and β,γ‐unsaturated α‐ketoesters, catalyzed by 0.2 mol% proline‐derived squaramide, delivers 3,4‐dihydropyranones in 74–98% yield with 90–99% ee within 4 h at ambient temperature. Combined NMR and computational studies characterize the product's keto‐enol tautomeric behavior, while synthetic applications include the diastereoselective construction of 3,4‐dihydropyranones featuring an all‐carbon quaternary stereocenter.

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来源期刊

Advanced Synthesis & Catalysis 化学-应用化学

CiteScore

9.40

自引率

7.40%

发文量

447

审稿时长

1.8 months

期刊介绍： Advanced Synthesis & Catalysis (ASC) is the leading primary journal in organic, organometallic, and applied chemistry. The high impact of ASC can be attributed to the unique focus of the journal, which publishes exciting new results from academic and industrial labs on efficient, practical, and environmentally friendly organic synthesis. While homogeneous, heterogeneous, organic, and enzyme catalysis are key technologies to achieve green synthesis, significant contributions to the same goal by synthesis design, reaction techniques, flow chemistry, and continuous processing, multiphase catalysis, green solvents, catalyst immobilization, and recycling, separation science, and process development are also featured in ASC. The Aims and Scope can be found in the Notice to Authors or on the first page of the table of contents in every issue.