Chemical Communications p. 1354 - 1357 (2016)
Update date:2022-08-16
Topics:
Rayner, Peter J.
Smith, Joshua C.
Denneval, Charline
O'Brien, Peter
Clarke, Paul A.
Horan, Richard A. J.
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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