Asymmetric Synthesis of 3-Pyrrole Substituted -Lactams Through p-Toluene sulphonic Acid-Catalyzed Reaction of azetidine-2,3-diones with Hydroxyprolines

IF 0.9 Q4 CHEMISTRY, PHYSICAL

Current Organocatalysis Pub Date : 2022-08-02 DOI:10.2174/2213337209666220802105301

R. N. Yadav, A. Shaikh, Aparna Das, D. Ray, B. Banik

引用次数: 0

Abstract

The aim of this study is to investigate the p-toluene sulphonic acid (p-Ts.OH) catalyzed reaction of racemic-azetidine-2,3-diones with enantiomerically pure cis and trans-4-hydroxy-L-proline in refluxing ethanol culminating in a synthesis of substituted novel 3-(pyrrol-1-yl)-azetidin-2-ones at the C-3 position. This work describes an alternative synthetic route enabling the tandem transformation of proline to pyrrole, followed by intramolecular chirality transfer to the -lactams ring. All four diastereomers of 3-(pyrrol-1-yl)-azetidin-2-ones could be achieved in good to excellent yield with high diastereoselectivity in a single-pot operation.

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3-吡咯取代物的不对称合成-对甲苯磺酸催化氮杂环丁烷-2,3-二酮与羟基脯氨酸反应制备乳酸

本研究的目的是研究对甲苯磺酸（p-Ts.OH）催化外消旋-氮杂环丁烷-2，3-二酮与对映体纯顺式和反式-4-羟基-L-脯氨酸在回流乙醇中的反应，最终在C-3位合成取代的新型3-（吡咯-1-基）-氮杂环丁-2-酮。这项工作描述了一种替代的合成路线，使脯氨酸能够串联转化为吡咯，然后分子内手性转移到-内酰胺环。3-（吡咯-1-基）-氮杂环丁烷-2-酮的所有四种非对映异构体都可以在一锅操作中以良好到优异的产率和高的非对映选择性获得。

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 Organocatalysis CHEMISTRY, PHYSICAL-

CiteScore

2.00

自引率

0.00%

发文量

期刊介绍： Current Organocatalysis is an international peer-reviewed journal that publishes significant research in all areas of organocatalysis. The journal covers organo homogeneous/heterogeneous catalysis, innovative mechanistic studies and kinetics of organocatalytic processes focusing on practical, theoretical and computational aspects. It also includes potential applications of organocatalysts in the fields of drug discovery, synthesis of novel molecules, synthetic method development, green chemistry and chemoenzymatic reactions. This journal also accepts papers on methods, reagents, and mechanism of a synthetic process and technology pertaining to chemistry. Moreover, this journal features full-length/mini review articles within organocatalysis and synthetic chemistry. It is the premier source of organocatalysis and synthetic methods related information for chemists, biologists and engineers pursuing research in industry and academia.