Asymmetric Synthesis of Substituted Thiolanes through Domino Thia‐Michael–Henry Dynamic Covalent Systemic Resolution using Lipase Catalysis

Dynamic systems based on consecutive thia‐Michael and Henry reactions were generated and transformed using lipase‐catalyzed asymmetric transformation. Substituted thiolane structures with three contiguous stereocenters were resolved in the process in high yields and high enantiomeric excesses.

     

Direct Asymmetric Dynamic Kinetic Resolution by Combined Lipase Catalysis and Nitroaldol (Henry) Reaction

The asymmetric synthesis of β‐nitroalkanol derivatives was simply achieved by a combined nitroaldol (Henry) reaction with lipase‐catalyzed transesterification in high yield and enantiomeric purity (up to 92% and 99% ee) through a direct one‐pot procedure.