The barrier to enantiomerization and dynamic resolution of N-Boc-2-lithiopiperidine and the effect of TMEDA
by Coldham, Iain; Leonori, Daniele; Beng, Timothy Kum; Gawley, Robert E.
The kinetics of enantiomerization and dynamic thermodynamic resolution (DTR) of N-Boc-2-lithiopiperidine have been measured, revealing significant differences in enthalpy and entropy for these processes and a role for the achiral ligand TMEDA; the racemization and the DTR are catalytic and first order in [TMEDA], and this has implications for asymmetric synthesis with chiral organolithiums.
- Journal
- Chemical Communications
- Issue
- 35
- Year
- 2009
- Start Page
- 5239
- ISBN/ISSN
- 1364-548X; 1359-7345
- PMID
- 19707632
- DOI
- 10.1039/b911024k