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Issue 35, 2009
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The barrier to enantiomerization and dynamic resolution of N-Boc-2-lithiopiperidine and the effect of TMEDA

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Abstract

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.

Graphical abstract: The barrier to enantiomerization and dynamic resolution of N-Boc-2-lithiopiperidine and the effect of TMEDA

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The article was received on 04 Jun 2009, accepted on 22 Jul 2009 and first published on 06 Aug 2009


Article type: Communication
DOI: 10.1039/B911024K
Citation: Chem. Commun., 2009,0, 5239-5241
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    The barrier to enantiomerization and dynamic resolution of N-Boc-2-lithiopiperidine and the effect of TMEDA

    I. Coldham, D. Leonori, T. K. Beng and R. E. Gawley, Chem. Commun., 2009, 0, 5239
    DOI: 10.1039/B911024K

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