Polyacrylic Acid Supported L-proline as an Effective Heterogeneous Catalyst for the Direct Asymmetric Aldol Reaction.

IF 1.7 4区化学 Q3 CHEMISTRY, ORGANIC

Current organic synthesis Pub Date : 2023-03-30 DOI:10.2174/1570179420666230330085329

Cuizhi Zhang, Yanchao Fan, Sijia Wang, Shaojie Liu, Xiaomeng Chu, Erjun Tang

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引用次数: 0

Abstract

Introduction: L-proline is an efficient chiral small-molecule organocatalyst for the direct asymmetric aldol reaction between unmodified acetone and a variety of aldehydes.

Method: However, it is difficult to separate from the reaction medium for reuse. In this work, polyacrylic acid (PAA) supported The acylation reaction between L-hydroxyproline and PAA prepared l-proline (P(AA-co-PA)) catalysts with various catalyst loadings. Fourier characterized them transforms infrared spectroscopy, nuclear magnetic resonance spectrum, gel permeation chromatography and thermogravimetry analysis.

Result: These macromolecular catalysts were used to catalyze acetone and benzaldehydes' direct asymmetric aldol reaction. The influence of the catalyst structure on the catalytic performance was studied, and the reaction conditions were optimized.

Conclusion: The results showed that P(AA-co-PA) with 50 mol% catalyst loading had excellent catalytic performance, much higher than that of L-proline and L-hydroxyproline. Its recovery was achieved by simple filtration. After being reused 7 times, its catalytic performance was still higher than that of L-proline.

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聚丙烯酸负载l -脯氨酸作为直接不对称醛醇反应的有效非均相催化剂。

l-脯氨酸是一种高效的手性小分子有机催化剂，用于未修饰的丙酮与多种醛直接发生不对称醛醇反应。方法:但从反应介质中分离再利用困难。本研究以聚丙烯酸(PAA)为载体，制备了l-羟脯氨酸(P(AA-co-PA))催化剂。傅里叶变换红外光谱、核磁共振光谱、凝胶渗透色谱和热重分析对其进行了表征。结果:这些大分子催化剂用于催化丙酮与苯甲醛的直接不对称醛反应。研究了催化剂结构对催化性能的影响，优化了反应条件。结论:负载50 mol%催化剂的P(AA-co-PA)具有优异的催化性能，远高于l -脯氨酸和l -羟脯氨酸。它的回收是通过简单的过滤。重复使用7次后，其催化性能仍高于l -脯氨酸。

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

Current organic synthesis 化学-有机化学

CiteScore

3.40

自引率

5.60%

发文量

审稿时长

6-12 weeks

期刊介绍： Current Organic Synthesis publishes in-depth reviews, original research articles and letter/short communications on all areas of synthetic organic chemistry i.e. asymmetric synthesis, organometallic chemistry, novel synthetic approaches to complex organic molecules, carbohydrates, polymers, protein chemistry, DNA chemistry, supramolecular chemistry, molecular recognition and new synthetic methods in organic chemistry. The frontier reviews provide the current state of knowledge in these fields and are written by experts who are internationally known for their eminent research contributions. The journal is essential reading to all synthetic organic chemists. Current Organic Synthesis should prove to be of great interest to synthetic chemists in academia and industry who wish to keep abreast with recent developments in key fields of organic synthesis.