Development of asymmetric syntheses of novel atropisomeric compounds

ORGN 53

Jonathan Clayden, clayden@manchester.ac.uk, School of Chemistry, The University of Manchester, Manchester, M13 9PL, United Kingdom and Wesley J. Moran, wesley.moran@manchester.ac.uk, School of Chemistry, The University of Manchester, Manchester, M13 9PL, United Kingdom.
Atropisomeric molecules have achieved remarkable success as chiral ligands for metals. Additionally, a number of important biological molecules exhibit atropisomerism, including the vancomycin/teicoplanin family of antibiotics. In others, such as the marine bastadins, which have a range of biological activities, the potential for atropisomerism remains unresolved. Notably, the vast majority of atropisomers that have been studied to date have been carbocyclic biaryls. Yet these form only one of dozens of conceivable families of atropisomers, any of which may offer at least as many benefits in the fields of biology or catalysis as the biaryls themselves. Research aimed at the asymmetric preparation of new families of compounds, diaryl ethers in particular, that exhibit atropisomerism will be revealed. Synthetic strategies including metal-catalyzed cycloadditions and dynamic thermodynamic resolutions will be discussed. In addition, the synthesis and utility of a chiral analog of the diaryl ether bis-phosphine ligand DPEphos will be outlined.