Synthesis of 1- and 4-substituted piperazin-2-ones via Jocic-type reactions with N-substituted diaminesElectronic supplementary information (ESI) available: Synthesis details, NMR spectra, chiral HPLC chromatograms and crystallographic details. CCDC 1022612-1022614. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c4ob02311k

Enantiomerically-enriched trichloromethyl-containing alcohols, obtained by asymmetric reduction, can be transformed regioselectively into 1-substituted piperazinones by modified Jocic reactions with little or no loss of stereochemical integrity. This methodology can be easily used to synthesise important pharmaceutical compounds such as the fluorobenzyl intermediate of a known PGGTase-I inhibitor. Enantiomerically-enriched trichloromethyl-containing alcohols are transformed regioselectively into enantiomerically-enriched 1-substituted piperazinones by modified Jocic reactions.