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

David M. Hodgson*, Christopher I. Pearson and Madiha Kazmi

*Department of Chemistry, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA, U.K., Email: david.hodgsonchem.ox.ac.uk

D. M. Hodgson, C. I. Pearson, M. Kazmi, Org. Lett., 2014, 16, 856-859.

DOI: 10.1021/ol403626k


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Abstract

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.

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Key Words

2-Azetines


ID: J54-Y2014