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

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JournalChemical Communications
DateE-pub ahead of print - 27 Nov 2015
DatePublished (current) - 25 Jan 2016
Issue number7
Volume52
Number of pages4
Pages (from-to)1354-1357
Early online date27/11/15
Original languageEnglish

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.

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