Rapid synthesis of macrocycles from diol precursors

Abstract

A method for the formation of synthetic macrocycles with different ring sizes from diols is presented. Reacting a simple diol precursor with electrophilic reagents leads to a cyclic carbonate, sulfite, or phosphate in a single step in 25–60% yield. Converting the cyclization precursor to a bis-electrophilic iodide or aldehyde enables preparation of a cyclic sulfide and amine, respectively, the latter using a double-reductive amination to induce ring closure.