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Generation and electrophile trapping of N-Boc-2-lithio-2-azetine: synthesis of 2-substituted 2-azetines.

ABSTRACT: s-BuLi-induced ?-lithiation-elimination of LiOMe from N-Boc-3-methoxyazetidine and further in situ ?-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.

SUBMITTER: Hodgson DM

PROVIDER: S-EPMC3929120 | biostudies-literature | 2014 Feb

REPOSITORIES: biostudies-literature

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Generation and electrophile trapping of N-Boc-2-lithio-2-azetine: synthesis of 2-substituted 2-azetines.

Hodgson David M DM Pearson Christopher I CI Kazmi Madiha M

Organic letters 20140110 3

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. ...[more]

PMID: 24410016

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