Diacetone glucose architecture as a chirality template I. Crucial effects of the intramolecular oxygens upon the LiAlH 4 reduction of the propargyl alcohol of 3- C-ethynyl-1,2:5,6-di- O-isopropylidene-α- D-allofuranose derivatives

Abstract

The facile as well as regio- and stereoselective reactivity of 3-C-ethynyl-1,2:5,6-di-O-isopropylidene-α-D-allofuranose derivatives for LiAlH 4 reduction into the corresponding ethenyl derivatives were investigated. The effect of oxygen atoms on the reduction is discussed by means of semi-empirical MO calculation.