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Issue 1, 2008
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The barrier to enantiomerization of N-Boc-2-lithiopyrrolidine: the effect of chiral and achiral diamines

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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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Publication details

The article was received on 20 Sep 2007, accepted on 03 Nov 2007 and first published on 15 Nov 2007


Article type: Communication
DOI: 10.1039/B714302H
Citation: Chem. Commun., 2008,0, 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, 0, 97
    DOI: 10.1039/B714302H

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