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
ID: J54-Y2014