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

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卷 25, 期 37, 页码 6813-6817

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AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.3c02284

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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.
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.

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