Copper-Catalyzed Direct Asymmetric Aldol Reaction of Glycine Schiff Bases to Access syn-β-Hydroxy-α-amino Esters

Org Lett. 2024 Sep 20;26(37):7981-7986. doi: 10.1021/acs.orglett.4c03085. Epub 2024 Sep 10.

Abstract

This study reported a copper-catalyzed direct asymmetric aldol reaction between aldehydes and glycine Schiff bases with methyl, allyl, and tert-butyl esters. Additionally, this reaction afforded high yields of syn-β-hydroxy-α-amino esters with excellent enantio- and diastereoselectivities (93-99% ee, up to >99:1 dr). The aldol reaction accepted aromatic, linear aliphatic, and α-substituted aliphatic aldehydes.