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Current Organocatalysis

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ISSN (Online): 2213-3380

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Research Article

Asymmetric Synthesis of 3-Pyrrole Substituted β-Lactams Through p-Toluene Sulphonic Acid-catalyzed Reaction of Azetidine-2,3-diones with Hydroxyprolines

Author(s): Ram Naresh Yadav, Aarif Latif Shaikh, Aparna Das, Devalina Ray and Bimal Krishna Banik*

Volume 9, Issue 4, 2022

Published on: 27 October, 2022

Page: [337 - 345] Pages: 9

DOI: 10.2174/2213337209666220802105301

Price: $65

Abstract

Aims: 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.

Methods: This work describes an alternative synthetic route enabling the tandem transformation of proline to pyrrole, followed by intramolecular chirality transfer to the β -lactams ring.

Results: 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.

Conclusion: This method can be applied to other activated carbonyl compounds and functionalized pyrroles can be obtained through an expeditious process.

Keywords: -lactam, L-proline, Staudinger reaction, Pyrrole, Anti-cancer

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