title: Kinetic resolution of 1,1'-biaryl-2,2'-diols and amino alcohols through NHC-catalyzed atroposelective acylation.
abstract: We present here a highly efficient NHC-catalyzed kinetic resolution of a wide range of 1,1'-biaryl-2,2'-diols and amino alcohols to provide them in uniformly ≥99% ee. This represents the first highly enantioselective catalytic acylation of axially chiral alcohols. The aldehyde backbone that is incorporated into the chiral acyl azolium intermediate was found to have a significant effect on the enantioselectivity of the process.
authors.affiliation: Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore 117543 (Singapore) http://zhaoyu.science.nus.edu.sg.
authors.forename: Shenci
authors.initials: S
authors.lastname: Lu
authors.forename: Si Bei
authors.initials: SB
authors.lastname: Poh
authors.forename: Yu
authors.initials: Y
authors.lastname: Zhao
mesh_terms: D000215:Acylation; D000605:Amino Alcohols / Q000737:chemistry*; D002384:Catalysis; D006571:Heterocyclic Compounds / Q000737:chemistry*; D007700:Kinetics; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D009284:Naphthols / Q000737:chemistry; D009584:Nitrogen / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000605:Amino Alcohols; C406944:BINOL, naphthol; D006571:Heterocyclic Compounds; D009284:Naphthols; C030011:carbene; D009584:Nitrogen; D008697:Methane
keywords: N-heterocyclic carbene; acylation; axial chirality; enantioselectivity; kinetic resolution