Synthesis of optically active heterocyclic compounds by preparation of 1,3-dinitro derivatives and enzymatic enantioselective desymmetrization of prochiral diamines

Article abstract of DOI:10.1002/ejoc.200900875

A 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).