Organocatalytic Enantioselective Synthesis of α-Hydroxyketones through a Friedel-Crafts Reaction of Naphthols and Activated Phenols with Aryl- and Alkylglyoxal Hydrates

Org Lett. 2016 Nov 4;18(21):5652-5655. doi: 10.1021/acs.orglett.6b02893. Epub 2016 Oct 25.

Abstract

An efficient organocatalytic asymmetric synthesis of α-hydroxyketones has been developed. Quinine-derived thiourea catalyzed the enantioselective Friedel-Crafts alkylation of naphthols and activated phenols with aryl- and alkylglyoxal hydrates, providing the corresponding chiral α-hydroxyketones with high yields (up to 97%) and excellent enantioselectivities (up to 99% ee).

Publication types

  • Research Support, Non-U.S. Gov't