title: Silver(I)-Catalyzed Diastereoselective Synthesis of anti-1,2-Hydroxyboronates.
abstract: A catalytic protocol for the diastereoselective synthesis of anti-1,2-hydroxyboronates is described. The process provides access to secondary alkyl organoborons. The deborylative 1,2-addition reactions of alkyl 1,1-diborons proceed in the presence of a silver(I) salt with either KOtBu or nBuLi as an activator. The catalytic diastereoselective protocol can be extended to aryl, alkenyl, and alkyl aldehydes with up to 99:1 d.r.
authors.affiliation: Department of Chemistry, The University of North Carolina at Chapel Hill, Chapel Hill, NC 27599-3290 (USA).
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, NC 27599-3290 (USA).
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, NC 27599-3290 (USA).
authors.forename: Matthew J
authors.initials: MJ
authors.lastname: Goldfogel
authors.affiliation: Department of Chemistry, The University of North Carolina at Chapel Hill, Chapel Hill, NC 27599-3290 (USA). sjmeek@unc.edu.
authors.forename: Simon J
authors.initials: SJ
authors.lastname: Meek
keywords: alcohols; asymmetric catalysis; boron; diastereoselectivity; silver