title: Copper(I)-catalyzed enantioselective nucleophilic borylation of aldehydes: an efficient route to enantiomerically enriched α-alkoxyorganoboronate esters.
abstract: The first catalytic enantioselective nucleophilic borylation of a C═O double bond has been achieved. A series of aldehydes reacted with a diboron reagent in the presence of a copper(I)/DTBM-SEGPHOS complex catalyst using MeOH as a proton source to give the corresponding optically active α-alkoxyorganoboronate esters with excellent enantioselectivities. Furthermore, the products could be readily converted to the corresponding functionalized chiral alcohol derivatives through stereospecific C-C bond forming reactions involving the stereogenic C-B bond.
authors.affiliation: Division of Chemical Process Engineering & Frontier Chemistry Center, Graduate School of Engineering, Hokkaido University , Sapporo, Hokkaido 060-8628, Japan.
authors.forename: Koji
authors.initials: K
authors.lastname: Kubota
authors.forename: Eiji
authors.initials: E
authors.lastname: Yamamoto
authors.forename: Hajime
authors.initials: H
authors.lastname: Ito
mesh_terms: D000447:Aldehydes / Q000138:chemical synthesis / Q000737:chemistry*; D001897:Boronic Acids / Q000138:chemical synthesis / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D004952:Esters / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D001897:Boronic Acids; D004952:Esters; D003300:Copper