Dynamics of Catalytic
Resolution of 2‑Lithio‑<i>N</i>‑Boc-piperidine
by Ligand Exchange
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Abstract
The dynamics of the racemization and catalytic and stoichiometric
dynamic resolution of 2-lithio-<i>N</i>-Boc-piperidine (<b>7</b>) have been investigated. The kinetic order in tetramethylethylenediamine
(TMEDA) for both racemization and resolution of the title compound
and the kinetic orders in two resolving ligands have been determined.
The catalytic dynamic resolution is second order in TMEDA and 0.5
and 0.265 order in chiral ligands <b>8</b> and <b>10</b>, respectively. The X-ray crystal structure of ligand <b>10</b> shows it to be an octamer. Dynamic NMR studies of the resolution
process were carried out. Some of the requirements for a successful
catalytic dynamic resolution by ligand exchange have been identified