Issue 1, 2008
From the journal:

Chemical Communications

The barrier to enantiomerization of N-Boc-2-lithiopyrrolidine: the effect of chiral and achiral diamines†

Taher I. Yousaf,a   Roger L. Williams,ab   Iain Coldhamc  and  Robert E. Gawley*a  

* Corresponding authors

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

b Eastern New Mexico University, Portales, NM, USA

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

Abstract

(−)-Sparteine and TMEDA dramatically lower both enthalpy and entropy of activation for the barrier to enantiomerization of N-Boc-2-lithiopyrrolidine in diethyl ether, whereas N,N′-diisopropyl bispidine has little effect; the entropy of activation for enantiomerization is zero in the presence of TMEDA and slightly negative in the presence of sparteine; these data suggest a subtle change in mechanism of enantiomerization in the presence of TMEDA and sparteine.

Graphical abstract: The barrier to enantiomerization of N-Boc-2-lithiopyrrolidine: the effect of chiral and achiral diamines

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Article information

DOI
https://doi.org/10.1039/B714302H
Article type
Communication
Submitted
20 Sep 2007
Accepted
03 Nov 2007
First published
15 Nov 2007

Chem. Commun., 2008, 97-98

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The barrier to enantiomerization of N-Boc-2-lithiopyrrolidine: the effect of chiral and achiral diamines

T. I. Yousaf, R. L. Williams, I. Coldham and R. E. Gawley, Chem. Commun., 2008, 97 DOI: 10.1039/B714302H

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