Issue 35, 2009
From the journal:

Chemical Communications

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

Iain Coldham,*a   Daniele Leonori,a   Timothy K. Bengb  and  Robert E. Gawley*b  

* Corresponding authors

a Department of Chemistry, University of Sheffield, Sheffield, UK
E-mail: i.coldham@sheffield.ac.uk
Fax: +44 (0)114 222 9346
Tel: +44 (0)114 222 9428

b Department of Chemistry and Biochemistry, University of Arkansas, Fayetteville, USA
E-mail: bgawley@uark.edu
Fax: +1 479 575 5178
Tel: +1 479 575 6933

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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DOI
https://doi.org/10.1039/B911024K
Article type
Communication
Submitted
04 Jun 2009
Accepted
22 Jul 2009
First published
06 Aug 2009

Chem. Commun., 2009, 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, 5239 DOI: 10.1039/B911024K

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