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

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.

Abstract