Synthesis of Optically Active Heterocyclic Compounds by Preparation of 1,3‐Dinitro Derivatives and Enzymatic Enantioselective Desymmetrization of Prochiral Diamines

Abstract

AbstractA general approach for the highly efficient chemical preparation of novel optically active 2‐substituted propane‐1,3‐diamines is described. Diamines have been obtained from the corresponding commercially available aldehydes in a straightforward two‐step synthesis via the corresponding 1,3‐dinitro compounds, which were hydrogenated under mild reaction conditions by using platinum dioxide as the catalyst. Subsequent enzymatic enantioselective desymmetrization mediated by Pseudomonas cepacia lipase allowed the recovery of a family of monocarbamates in good to high enantiomeric excesses (70–90 % ee).