Synthesis of atropisomeric diamides with remotely related stereogenic axes by stereoselective additions to imines

Atroposelective addition of axially chiral laterally lithiated 2-alkyl- 1-naphthamides to 6-substituted 2-(N-methylformimino)benzamides leads, after equilibration of the new stereogenic axis to its more stable conformation, to single atropisomeric diastereoisomers of diamides bearing remotely related stereogenic axes separated by one or two stereogenic centres. The newly created MeNH-bearing stereogenic centre 'relays' stereochemical information from the first axis to the second.