First Asymmetric Synthesis of Passerini‐Type Condensation Products in Water Using Pregabalin: A Chiral Amino Acid for the Efficient Asymmetric Induction

Abstract

AbstractThis article describes the use of Pregabalin as a commercially available chiral amino acid in the efficient synthesis of the Passerini‐type condensation products via two‐component condensation of aromatic aldehydes with cyclohexyl isocyanide. All reactions are accompanied with aerobic oxidation of aldehydes in water leading to chiral α‐acyloxycarboxamides with moderate to good enantioselectivities (up to 88 % ee) under green conditions such as nonmetal source. This is the first report of asymmetric synthesis of Passerini products in water.