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Abstract
Abstract Deprotonation of N -Boc- N ′-alkylpiperazines with sec -BuLi in Et 2 O–TMEDA gave the 2-lithio derivatives which were resolved in the presence of a chiral ligand. The best ligands for the asymmetric substitution were diamino-alkoxides that promoted a dynamic thermodynamic resolution (DTR) of the organolithium at −30 °C. Electrophilic quench gave enantiomerically enriched 2-substituted piperazines. Of a selection of piperazines, the N ′- t -butyl derivative gave the best results, with the product N -Boc- N ′- t -butyl-2-substituted piperazines being formed with enantiomer ratios up to 81:19.
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