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

Atroposelective addition of axially chiral laterally lithiated 2-alkyl-1-na phthamides to 6-substituted 2-(N-methylformimino)benzamides leads, after eq uilibration 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 cr eated MeNH-bearing stereogenic centre "relays" stereochemical information f rom the first axis to the second. (C) 1999 Elsevier Science Ltd. All rights reserved.