Catechol-derived propargyl diol cyclizations with malonyl dichloride: substituent effects on the formation of macrocyclic esters and their hydrochlorinated adducts

George Lefkaritis; Andreas Kourtellaris; Nikos Chronakis; Savvas N. Georgiades

doi:10.1039/d5ra09108j

January 1, 2026RSC AdvancesOpen Access

Catechol-derived propargyl diol cyclizations with malonyl dichloride: substituent effects on the formation of macrocyclic esters and their hydrochlorinated adducts

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Key Points

The research aims to explore how substituents on catechol-derived propargyl diols influence macrocyclization outcomes when reacting with malonyl dichloride.
Conducted macrocyclization reactions of catechol-derived propargyl diols with malonyl dichloride.
Evaluated differing hydroxy protecting groups to assess their effects on product distribution.
Analyzed the (stereo)electronic influences of electron-donating vs. electron-withdrawing groups.
Successfully synthesized macrocyclic esters and their hydrochlorinated counterparts.
Identified distinct product distributions influenced by the nature of hydroxy protecting groups.
Demonstrated variations in reactivity based on electron-donating and electron-withdrawing characteristics.

Implication

Macrocyclization demonstrates substituent effects on product distribution in catechol-derived compounds, suggesting new pathways for synthesis.

Abstract

Macrocyclization of catechol-derived propargyl diols with malonyl dichloride revealed (stereo)electronic effects of hydroxy protecting groups, dictating alternative product distributions in ED vs. EW cases.

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Cite This Study

Lefkaritis et al. (2026) studied this question.

synapsesocial.com/papers/69db38534fe01fead37c6853 https://doi.org/10.1039/d5ra09108j

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Catechol-derived propargyl diol cyclizations with malonyl dichloride: substituent effects on the formation of macrocyclic esters and their hydrochlorinated adducts

Key Points

Implication

Abstract

Discussion

Cite This Study

Catechol-derived propargyl diol cyclizations with malonyl dichloride: substituent effects on the formation of macrocyclic esters and their hydrochlorinated adducts

Key Points

Implication

Abstract

Discussion

Cite This Study

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