Reversible aryl migrations in metallated ureas: Controlled inversion of configuration at a quaternary carbon atom

Daniel J. Tetlow, Mark A. Vincent, Ian H. Hillier, Jonathan Clayden*

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

13 Citations (Scopus)

Abstract

Deprotonation with strong bases of N-vinyl ureas carrying an N′-aryl substituent leads to migration of the N′-aryl group from N to C via an allyllithium; with weaker bases and electron-deficient aryl rings the direction of the migration reverses, and aryl substituents α to the urea N atom may migrate from C to N.

Original languageEnglish
Pages (from-to)1548-1550
Number of pages3
JournalChemical Communications
Volume49
Issue number15
Early online date3 Jan 2013
DOIs
Publication statusPublished - 21 Feb 2013

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