title: Facile formation of β-hydroxyboronate esters by a Cu-catalyzed diboration/Matteson homologation sequence.
abstract: The copper-catalyzed diboration of aldehydes was used in conjunction with the Matteson homologation, providing the efficient synthesis of β-hydroxyboronate esters. The oxygen-bound boronate ester was found to play a key role in mediating the homologation reaction, which was compared to the α-hydroxyboronate ester (isolated hydrolysis product). The synthetic utility of the diboration/homologation sequence was demonstrated through the oxidation of one product to provide a 1,2-diol.
authors.affiliation: ‡Department of Chemistry, Western Washington University, 516 High Street Bellingham, Washington 98225, United States.
authors.forename: Cameron M
authors.initials: CM
authors.lastname: Moore
authors.affiliation: †Department of Chemistry and Biochemistry, University of San Diego, 5998 Alcala Park, San Diego, California 92110, United States.|‡Department of Chemistry, Western Washington University, 516 High Street Bellingham, Washington 98225, United States.
authors.forename: Casey R
authors.initials: CR
authors.lastname: Medina
authors.affiliation: †Department of Chemistry and Biochemistry, University of San Diego, 5998 Alcala Park, San Diego, California 92110, United States.
authors.forename: Peter C
authors.initials: PC
authors.lastname: Cannamela
authors.affiliation: ‡Department of Chemistry, Western Washington University, 516 High Street Bellingham, Washington 98225, United States.
authors.forename: Melissa L
authors.initials: ML
authors.lastname: McIntosh
authors.affiliation: †Department of Chemistry and Biochemistry, University of San Diego, 5998 Alcala Park, San Diego, California 92110, United States.
authors.forename: Carl J
authors.initials: CJ
authors.lastname: Ferber
authors.affiliation: †Department of Chemistry and Biochemistry, University of San Diego, 5998 Alcala Park, San Diego, California 92110, United States.
authors.forename: Andrew J
authors.initials: AJ
authors.lastname: Roering
authors.affiliation: †Department of Chemistry and Biochemistry, University of San Diego, 5998 Alcala Park, San Diego, California 92110, United States.
authors.forename: Timothy B
authors.initials: TB
authors.lastname: Clark
mesh_terms: D000438:Alcohols / Q000138:chemical synthesis / Q000737:chemistry; D000447:Aldehydes / Q000737:chemistry*; D001897:Boronic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D004952:Esters; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013237:Stereoisomerism
chemical_list: D000438:Alcohols; D000447:Aldehydes; D001897:Boronic Acids; D004952:Esters; D003300:Copper