title: Asymmetric synthesis of protected α-amino boronic acid derivatives with an air- and moisture-stable Cu(II) catalyst.
abstract: The asymmetric borylation of N-tert-butanesulfinyl imines with bis(pinacolato)diboron is achieved using a Cu(II) catalyst and provides access to synthetically useful and pharmaceutically relevant α-amino boronic acid derivatives. The Cu(II)-catalyzed reaction is performed on the benchtop in air at room temperature using commercially available, inexpensive reagents at low catalyst loadings. A variety of N-tert-butanesulfinyl imines, including ketimines, react readily to provide α-sulfinamido boronate esters in good yields and with high stereoselectivity. In addition, this transformation is applied to the straightforward, telescoped synthesis of α-sulfinamido trifluoroborates.
authors.affiliation: Department of Chemistry, Yale University , 225 Prospect Street, New Haven, Connecticut 06520-8107, United States.
authors.forename: Andrew W
authors.initials: AW
authors.lastname: Buesking
authors.forename: Vlad
authors.initials: V
authors.lastname: Bacauanu
authors.forename: Irene
authors.initials: I
authors.lastname: Cai
authors.forename: Jonathan A
authors.initials: JA
authors.lastname: Ellman
mesh_terms: D001881:Borates / Q000138:chemical synthesis*; D001896:Boron Compounds / Q000737:chemistry*; D001897:Boronic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D002074:Butanones / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D007097:Imines / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism; D013449:Sulfonamides / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D001881:Borates; D001896:Boron Compounds; D001897:Boronic Acids; D002074:Butanones; D007097:Imines; D013449:Sulfonamides; C463639:bis(pinacolato)diboron; D003300:Copper; C098759:fluoroboric acid