Generation and Electrophile Trapping of N-Boc-2-lithio-2-azetine: Synthesis of 2-Substituted 2-Azetines

[Image: see text] s-BuLi-induced α-lithiation–elimination of LiOMe from N-Boc-3-methoxyazetidine and further in situ α-lithiation generates N-Boc-2-lithio-2-azetine which can be trapped with electrophiles, either directly (carbonyl or heteroatom electrophiles) or after transmetalation to copper (all...

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Detalles Bibliográficos
Autores principales: Hodgson, David M., Pearson, Christopher I., Kazmi, Madiha
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2014
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3929120/
https://www.ncbi.nlm.nih.gov/pubmed/24410016
http://dx.doi.org/10.1021/ol403626k
Descripción
Sumario:[Image: see text] s-BuLi-induced α-lithiation–elimination of LiOMe from N-Boc-3-methoxyazetidine and further in situ α-lithiation generates N-Boc-2-lithio-2-azetine which can be trapped with electrophiles, either directly (carbonyl or heteroatom electrophiles) or after transmetalation to copper (allowing allylations and propargylations), providing a concise access to 2-substituted 2-azetines.

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