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 describes the synthesis of 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 synthesis of (R)-pantolactone using only two synthetic steps.