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Synthesis of 2-azetines

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α-Lithiation-elimination of LiOMe from N-Boc-3-methoxyazetidine in the presence of s-BuLi and subsequent in situ α-lithiation generates N-Boc-2-lithio-2-azetine which can either directly or after transmetalation to copper react with electrophiles, providing a concise access to 2-substituted 2-azetines.
D. M. Hodgson, C. I. Pearson, M. Kazmi, Org. Lett., 2014, 16, 856-859.


A one-pot Suzuki cross-coupling or a catalyst-free arylation enable a facile introduction of aryl and heteroaryl substituents on the azetine skeleton at the position α to the nitrogen.
A. N. Baumann, M. Eisold, A. Music, G. Haas, Y. M. Kiw, D. Didier, Org. Lett., 2017, 19, 5681-5684.