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
Lithiation-electrophilic substitution of N-thiopivaloylazetidine
Hodgson, David M.,Kloesges, Johannes
supporting information; experimental part, p. 2900 - 2903 (2010/06/19)
(Figure Presented) The fourth protocol: The rarely studied Nthiopivaloyl group plays a crucial role in mediating efficient ∞ lithiation and incorporation of diverse electrophiles onto an azetidine ring; in the presence of chiral ligands, this chemistry also provides the first example of an enantioselective electrophilic substitution on a four-membered ring.