4.6 Article

Synthesis of 1-Arylcycloalkenamines by Intramolecular Arylation of Lithiated Ureas

Journal

ORGANIC PROCESS RESEARCH & DEVELOPMENT
Volume 18, Issue 10, Pages 1245-1252

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/op500173q

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Funding

  1. EPSRC
  2. AstraZeneca
  3. Deutsche Forschungsgemeinschaft
  4. Royal Society Wolfson Research Merit Award

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The deprotonation of N'-arylurea derivatives of cyclohexenamines by alkyllithiums leads to migration of the N'-aryl substituent from N' to the allylic position alpha to N via rearrangement of a urea-stabilised allyllithium intermediate. The product ureas may be solvolysed to reveal 1-arylcydohexenamines.

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