Abstract: Five tertiary 2,3-epoxy alcohols with different structures and/or stereochemistry have been investigated on the reaction with aluminum isopropoxide(AIP), three of which were shown to undergo an unusual reductive rearrangement to form 1,3-diol products. Further investigation results about the substitution effects and the product's stereochemistry of this reaction were also discussed.

Key words: Epoxy alcohols, Rearrangement reaction, Stereocontrol