Synthesis of pure enantiomers of a new diol ligand, trans-4,5-Bis(2-hydroxyphenyl)-2,2-dimethyl-1,3-dioxolane

Abstract

A new chiral diol, trans-4,5-bis(2-hydroxyphenyl)-1,3-dioxolane, was synthesized by the reductive coupling of O-benzylated salicylaldehyde with a low-valent titanium reagent followed by acetalization and deprotection. Resolution of the diol was achieved through a sequence of esterification with O-methylmandelic acid, chromatographic separation and purification, and methanolysis.