1236273-03-2Relevant articles and documents
Dynamic thermodynamic resolution of lithiated N-Boc-N′- alkylpiperazines
Robinson, Steven P.,Sheikh, Nadeem S.,Baxter, Carl A.,Coldham, Iain
scheme or table, p. 3642 - 3644 (2010/09/05)
Deprotonation of N-Boc-N′-alkylpiperazines with sec-BuLi in Et 2O-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.