107020-12-2Relevant articles and documents
Mechanistic interrogation of the asymmetric lithiation-trapping of N-thiopivaloyl azetidine and pyrrolidine
Rayner, Peter J.,Smith, Joshua C.,Denneval, Charline,O'Brien, Peter,Clarke, Paul A.,Horan, Richard A. J.
, p. 1354 - 1357 (2016)
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.
Synthesis and Homologation of an Azetidin-2-yl Boronic Ester with α-Lithioalkyl Triisopropylbenzoates
Delany, Pascal K.,Hodgson, David M.
supporting information, p. 9981 - 9984 (2019/12/24)
An α-boryl azetidine, obtained by α-lithiation-borylation of N-Botc azetidine, undergoes reaction with α-triisopropylbenzoyloxy organolithiums to give homologated boronic esters that can be further oxidized, homologated, arylated, and deprotected to give
AZETIDINE COMPOUNDS AS OREXIN RECEPTOR ANTAGONISTS
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Page/Page column 24, (2010/09/07)
The invention relates to novel azetidine compounds of formula (I), wherein R1, R2, and X are as described in the description and their use as orexin receptor antagonists.
