title: Enantio- and Diastereoselective Synthesis of 1,2-Hydroxyboronates through Cu-Catalyzed Additions of Alkylboronates to Aldehydes.
abstract: The first catalytic enantio- and diastereoselective synthesis of 1,2-hydroxyboronates is reported. Reactions are promoted by a readily available chiral monodentate phosphoramidite-copper complex in the presence of an alkyl 1,1-diboron reagent. Products contain two contiguous stereogenic centers and are obtained in up to 91% yield, >98:2 d.r., and 98:2 e.r. The reaction is tolerant of aryl and vinyl aldehydes, and the 1,2-hydroxyboronate products can be transformed into versatile derivatives. Mechanistic experiments indicate control of absolute stereochemistry of the α-boryl component.
authors.affiliation: Department of Chemistry, The University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599-3290, United States.
authors.forename: Matthew V
authors.initials: MV
authors.lastname: Joannou
authors.affiliation: Department of Chemistry, The University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599-3290, United States.
authors.forename: Brandon S
authors.initials: BS
authors.lastname: Moyer
authors.affiliation: Department of Chemistry, The University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599-3290, United States.
authors.forename: Simon J
authors.initials: SJ
authors.lastname: Meek
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D000478:Alkylation; D001897:Boronic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D006900:Hydroxylation; D009943:Organophosphorus Compounds / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D001897:Boronic Acids; D009943:Organophosphorus Compounds; C434331:phosphoramidite; D003300:Copper