Alexey V. Kurenkov

Synthesis and some features of phase behavior of chiral p-alkoxyphenyl glycerol ethers

A series of (S)-3-(4-alkoxyphenoxy)propane-1,2-diols was prepared with the enantiomeric excess 86–92% by Sharpless asymmetric dihydroxylation of 1-alkoxy-4-allyloxybenzenes with an AD-mix-β mixture. R-Enantiomers with enantiomeric excess 97–99% and racemic samples were obtained by reaction of sodium p-substituted phenolates with (R)- and rac-3-chloropropane-1,2-diol. The phase behavior of racemates and scalemates in the produced homolog series of glycerol aryl ethers with hydrocarbon substituents of various length was examined by means of thermomicroscopy. The higher memberes of the homolog series of both racemic and scalemic diols undergo at heating an enantiotropic phase transition to a smectic liquid crystal phase.

Synthesis of enantiomerically pure 3-aryloxy-2-hydroxypropanoic acids, intermediate products in the synthesis of cis-4-Aminochroman-3-ols

Oxidation of accessible (R)-3-chloropropane-1,2-diol to (R)-3-chloro-2-hydroxypropanoic acid and subsequent reaction of the latter with ortho-substituted sodium phenoxide gave a number of enantiomerically pure 3-aryloxy-2-hydroxypropanoic acid which are intermediate products in the synthesis of nonracemic 4-aminochroman-3-ols.