A series of enantiopure 2,2'-bipyridines have been synthesised from the corresponding cis-dihydrodiol metabolites of 2-chloroquinolines. Several of the resulting hydroxylated 2,2'-bipyridines were found to be useful chiral ligands for the asymmetric aminolysis of meso-epoxides leading to the formation of enantioenriched amino alcohols (-> 84%ee). N-oxide and N,N'-dioxide derivatives of these 2,2'-bipyridines, including separable atropisomers, have been synthesised and used as enantioselective organocatalysts in the asymmetric allylation of aldehydes to give allylic alcohols (-> 86%ee).
ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Organic Chemistry
Boyd, D., Sharma, N., Sbircea, L., Murphy, D., Malone, J., James, S. L., Allen, C., & Hamilton, J. (2010). Chemoenzymatic synthesis of chiral 2,2 '-bipyridine ligands and their N-oxide derivatives: applications in the asymmetric aminolysis of epoxides and asymmetric allylation of aldehydes. Organic and Biomolecular Chemistry, 8(5), 1081-1090. https://doi.org/10.1039/b919894f