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

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

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...

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Veröffentlicht in:Organic letters 2014-02, Vol.16 (3), p.856-859
Hauptverfasser: Hodgson, David M, Pearson, Christopher I, Kazmi, Madiha
Format: Artikel
Sprache:eng
Schlagworte:
allylation
Azetines - chemical synthesis
Azetines - chemistry
chemical structure
copper
Copper - chemistry
Letter
Lewis acids
Lithium - chemistry
Molecular Structure
organic compounds
Organometallic Compounds - chemical synthesis
Organometallic Compounds - chemistry
Stereoisomerism
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Zusammenfassung: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.
ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/ol403626k