Synthesis of 1-arylcycloalkenamines by intramolecular arylation of lithiated ureas

Michael B. Tait, Philipp A. Ottersbach, Daniel J. Tetlow, Jonathan Clayden*

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)

6 Citations (Scopus)

Abstract

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

Original languageEnglish
Pages (from-to)1245-1252
Number of pages8
JournalOrganic Process Research & Development
Volume18
Issue number10
Early online date21 Jul 2014
DOIs
Publication statusPublished - 17 Oct 2014

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