The stereoselective conversion of 2-alkenyl alcohols to (R)- or (S)- alkane-1, 2-diols using D-glucose as a chiral auxiliary

Article abstract of DOI:10.1016/S0040-4039(98)02472-1

The stereoselective addition of the 2-hydroxyl group of glucose to the mercurated vinyl group of 2-alkenyl glycosides followed by hydride reduction and removal of the saccharide fragment was used to prepare enantiomerically pure 1,2-dihydroxy alkanes. Diols of (R) or (S) configuration can be synthesized from (α)-glycosides or the (β) form respectively. Demercuration with chloride ion led to the insertion of a halo group adjacent to the new chiral center thus allowing for the possibility of further functionalization.