Enantioselectivity in enediol-hydroxyketone tautomerization

The conversion of racemic α-hydroxyketone into optically active α-hydroxyketone with e.e. as high as 80 % and in good yield is reported. This is accomplished by a low temperature enantioselective protonation of the enediol using (2R, 3R) O,O-dipivaloyltartaric acid.