Resin-Supported Peptide-Catalyzed Asymmetric Aldol Reaction of Aldehydes for the Synthesis of (R)-Pantolactone

Abstract

A highly enantioselective heterogeneous cross-aldol reaction between aldehydes and glyoxylates or α-ketoaldehydes has been achieved for the first time using resin-supported peptide catalysts. This study synthesizes various 1,4-dicarbonyl compounds, achieving excellent enantioselectivities and yields while using water and acetonitrile as solvents. The reaction can be conducted on a gram-scale, and the polystyrene aminomethyl-supported peptide can be reused in water without losing enantioselectivity. This work enables the potential industrial production of (R)-pantolactone using only two synthetic steps.