title: Diastereoselective synthesis of atropisomers containing two non-biaryl stereogenic axes: stereochemical relay through stereogenic centres in dihydrostilbene-2,2'-dicarboxamides.
abstract: Addition of laterally lithiated tertiary aromatic amides to benzaldimines controls the formation of a new stereogenic centre adjacent to the benzaldimine aromatic ring. Drawing on the fact that such amino-substituted stereogenic centres may themselves control the conformation of amides, with amido-substituted benzaldimines we found it becomes possible to relay stereochemistry from one amide to another via this intervening stereogenic centre. A group of dihydrostilbene-2,2'-dicarboxamide derivatives bearing one or two stereogenic axes are made by this method, which demonstrates the use of combined kinetic and thermodynamic control for the relay of stereochemical information.
authors.affiliation: School of Chemistry, University of Manchester, Oxford Road, Manchester, UKM13 9PL. clayden@man.ac.uk
authors.forename: Jonathan
authors.initials: J
authors.lastname: Clayden
authors.forename: Neil
authors.initials: N
authors.lastname: Westlund
authors.forename: Christopher S
authors.initials: CS
authors.lastname: Frampton
authors.forename: Madeleine
authors.initials: M
authors.lastname: Helliwell