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

摘要

This 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.