Dynamics of Catalytic Resolution of 2-Lithio-N-Boc-piperidine by Ligand Exchange

摘要

The dynamics of the racemization, catalytic and stoichiometric dynamic resolution of 2-lithio-N-Boc-piperidine, >7, have been investigated. The kinetic order in TMEDA, for both racemization and resolution of the title compound, and the kinetic order in resolving ligands, have been determined. The catalytic dynamic resolution is 0.5-order in chiral ligand >8, 0.265 order in chiral ligand >10, and second order in TMEDA. The X-ray crystal structure of ligand >10 shows it to be an octamer. Dynamic NMR studies of the resolution process were obtained. Some of the requirements for a successful catalytic dynamic resolution by ligand exchange have been identified.