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

Chem Commun (Camb). 2013 Feb 21;49(15):1548-50. doi: 10.1039/c2cc38704b.

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amides / chemistry
  • Amino Alcohols / chemistry
  • Carbon / chemistry*
  • Lithium / chemistry*
  • Nitrogen / chemistry
  • Urea / chemistry*

Substances

  • Amides
  • Amino Alcohols
  • Carbon
  • Urea
  • Lithium
  • Nitrogen