Enantioselective Friedel-Crafts Reaction of Heteroaromatic Compounds with Glyoxals Catalyzed by Chiral Oxazaborolidinium Ion Catalyst

A catalytic enantioselective Friedel-Crafts reaction of various heteroaromatic compounds with glyoxals has been developed. In the presence of a chiral oxazaborolidinium ion catalyst, the reaction provided chiral alpha-hydroxyketones in high yield (up to 96%) with excellent enantioselectivity (up to > 99% ee). The synthetic utility of this method was illustrated by conversion of the products to various derivatives such as 1,2-diol and ss-amino alcohol.

Automated summary

A catalytic enantioselective Friedel-Crafts reaction of various heteroaromatic compounds with glyoxals has been developed, providing chiral alpha-hydroxyketones in high yield and excellent enantioselectivity. The synthetic utility of this method was demonstrated by converting the products to various derivatives such as 1,2-diol and optically active amino alcohol.