Developments in Meyers' lactamization methodology: en route to bi(hetero)aryl structures with defined axial chirality

J Org Chem. 2013 Aug 16;78(16):8191-7. doi: 10.1021/jo401259w. Epub 2013 Aug 7.

Abstract

Highly atroposelective Meyers' lactamization promoted by pivalic acid under microwave irradiation is reported which allows the construction of nonracemic substituted-dibenzo(di)azepine derivatives through a center to axial chirality transfer principle, controlling the otherwise configurationally labile biaryl axis. This approach provides a straightforward entry to enantioenriched analogues of biorelevant architectures.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Azepines / chemical synthesis*
  • Azepines / chemistry
  • Microwaves
  • Molecular Conformation
  • Stereoisomerism

Substances

  • Azepines