Facile synthesis of C2-Symmetric chiral crown ethers with two reactive hydroxymethyl groups

Two C2-symmetric chiral crown ethers, (2S,12S)-2,12-bis(hydroxymethyl)-2,12-dimethyl-18-crown-6 and (2R,9R)-2,9bis(hydroxymethyl)-2,9-dimethyl-18-crown-6 were synthesized from a chiral subunit, [(4S)-2,2,4-trim( thyl-1,3-dioxolane-4yl]methanol, at high enantiomeric purity over several steps. This synthetic method offers the potential to construct a variety of C-2-symmetric chiral crown ethers using diverse combinations of building blocks.