A new synthetic route to (S)-chroman aldehyde, a key chiral precursor of vitamin E

Abstract

A highly stereocontrolled synthetic route to (S)-chroman aldehyde has been developed which starts with trimethyl-p-hydroquinone and (R)-glycerladehyde acetonide and employs as key steps the Michael addition of the aromatic copper species onto the (R)-4-acryloyl-1,3-dioxolane followed by the highly diastereoselective methylation of the resulting ketone adduct.