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Issue 7, 2016
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Mechanistic interrogation of the asymmetric lithiation-trapping of N-thiopivaloyl azetidine and pyrrolidine

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Abstract

A fundamental mechanistic study of the s-BuLi/chiral diamine-mediated lithiation-trapping of N-thiopivaloyl azetidine and pyrrolidine is reported. We show that lithiated thiopivalamides are configurationally unstable at −78 °C. Reaction then proceeds via a dynamic resolution of diastereomeric lithiated intermediates and this accounts for the variable sense and degree of asymmetric induction observed compared to N-Boc heterocycles.

Graphical abstract: Mechanistic interrogation of the asymmetric lithiation-trapping of N-thiopivaloyl azetidine and pyrrolidine

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Publication details

The article was received on 19 Oct 2015, accepted on 24 Nov 2015 and first published on 27 Nov 2015


Article type: Communication
DOI: 10.1039/C5CC08690F
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Chem. Commun., 2016,52, 1354-1357

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    Mechanistic interrogation of the asymmetric lithiation-trapping of N-thiopivaloyl azetidine and pyrrolidine

    P. J. Rayner, J. C. Smith, C. Denneval, P. O'Brien, P. A. Clarke and R. A. J. Horan, Chem. Commun., 2016, 52, 1354
    DOI: 10.1039/C5CC08690F

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