ChemInform Abstract: Asymmetric Synthesis of Chiral β‐Hydroxy‐α‐amino Acid Derivatives by Organocatalytic Aldol Reactions of Isocyanoesters with β,γ‐Unsaturated α‐Ketoesters.

Abstract

Abstract The first organocatalytic asymmetric aldol reaction of isocyanoesters with various β,γ-unsaturated α-ketoesters has been described. Using cinchona alkaloid-derived bifunctional thiourea as the catalyst, chiral β-hydroxy-α-amino acid derivatives can be obtained in excellent yields and enantioselectivities (up to 95% yield and 92% ee) after acidic hydrolysis. This protocol provides a straightforward method to access multiple substituted β-hydroxy-α-amino acid derivatives with high enantiomeric purity.