title: Kinetic resolution of α-substituted alkanoic acids promoted by homobenzotetramisole.
abstract: A new method for catalytic nonenzymatic kinetic resolution of α-substituted alkanoic acids has been developed, which relies on their activation with DCC followed by enantioselective alcoholysis of the intermediate symm-anhydrides in the presence of the amidine-based catalyst homobenzotetramisole (HBTM). Moderate to excellent selectivity factors (s=5-96) have been obtained in the case of several classes of substrates, namely, α-aryl-, α-aryloxy/alkoxy-, α-halo-, α-azido-, and α-phthalimido-alkanoic acids. Under similar conditions, α-(arylthio/alkylthio)-alkanoic acids undergo dynamic kinetic resolution providing corresponding esters in up to 92% ee and up to 93% yield.
authors.affiliation: Department of Chemistry, Washington University, Saint Louis, Missouri 63130, USA.
authors.forename: Xing
authors.initials: X
authors.lastname: Yang
authors.forename: Vladimir B
authors.initials: VB
authors.lastname: Birman
mesh_terms: D000143:Acids / Q000737:chemistry*; D000473:Alkanes / Q000737:chemistry*; D000812:Anhydrides / Q000737:chemistry*; D002384:Catalysis; D007700:Kinetics; D015394:Molecular Structure; D013237:Stereoisomerism; D013773:Tetramisole / Q000031:analogs & derivatives* / Q000737:chemistry
chemical_list: D000143:Acids; D000473:Alkanes; D000812:Anhydrides; C515434:benzotetramisole; D013773:Tetramisole