Journal
ORGANIC LETTERS
Volume 21, Issue 6, Pages 1818-1822Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.9b00407
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Funding
- Royal Society [RG150441, RGF\EA\180031]
- EPSRC
- AstraZeneca
- Imperial College London
- EPSRC [1850445] Funding Source: UKRI
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The ring expansion of 2-ester-2-arylazetidine carbamates can be achieved using Bronsted acids to form 6,6-disubstituted 1,3-oxazinan-2-ones. The reaction is rapid at room temperature with Boc or Cbz derivatives and proceeds with excellent yield (up to 96%) and broad substrate scope. Derivatives of drug compounds and natural products are incorporated. The combination of this ring expansion in a three-step N-H insertion/cyclization/expansion sequence is applied to directly access medicinally relevant scaffolds from acyclic precursors.
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