Diacetone glucose architecture as a chirality template I. Crucial effects of the intramolecular oxygens upon the LiAlH4 reduction of the propargyl alcohol of 3-C-ethynyl-1,2:5,6-di-O-isopropylidene-α-D-allofuranose derivatives

Article abstract of DOI:10.1016/S0040-4020(01)96152-6

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 LiAlH₄ 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.