Lipase-Catalyzed Cyclization of β-Ketothioamides with β-Nitrostyrene for the Synthesis of Tetrasubstituted Dihydrothiophenes

TL;DR

This paper presents a new eco-friendly method using lipase to efficiently create tetrasubstituted dihydrothiophenes, which are important in medicine and materials science.

Contribution

The study introduces a novel lipase-catalyzed synthesis method for tetrasubstituted dihydrothiophenes with high yields.

Findings

Sixteen tetrasubstituted dihydrothiophenes were synthesized with yields between 80% and 96%.

Porcine pancreatic lipase was shown to be effective beyond traditional hydrolytic reactions in organic synthesis.

The method provides an environmentally friendly alternative for producing these heterocyclic compounds.

Abstract

Tetrasubstituted dihydrothiophenes represent a class of heterocyclic compounds with significant potential in various fields, particularly in medicinal chemistry and materials science. In this work, we have developed an eco-friendly and efficient method for synthesizing such compounds, using porcine pancreatic lipase (PPL) as a biocatalyst to promote the cyclization reaction between β-ketothioamides and β-nitrostyrenes. Through this approach, sixteen tetrasubstituted dihydrothiophenes were successfully synthesized, and all of them achieved high yields, ranging from 80% to 96%. This research not only expands the application scope of lipase in organic synthesis, demonstrating its versatility beyond traditional hydrolytic reactions, but also provides a new environmentally friendly pathway for the production of tetrasubstituted dihydrothiophenes, which is of great significance for advancing related fields of chemical synthesis.

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