title: Nickel-Catalyzed Double Bond Transposition of Alkenyl Boronates for in Situ syn-Selective Allylboration Reactions.
abstract: The transposition of a homoallyl pinacol boronic ester was realized by a highly reactive nickel-catalyst system comprising NiCl2(dppp), zinc powder, ZnI2, and Ph2PH. The in situ generated Z-crotyl pinacol boronic esters were reacted with various aldehydes to form syn-homoallylic alcohols in high diastereoselectivities. The present nickel-catalyzed reaction is complementary to the iridium-catalyzed transposition reported by Murakami leading to the corresponding anti-homoallylic alcohols. Also, the multiple transposition of pentenyl pinacol boronic ester was realized.
authors.affiliation: Fachbereich Chemie, Philipps-Universität Marburg , Hans-Meerwein-Straße 4, D-35043 Marburg, Germany.
authors.forename: Felicia
authors.initials: F
authors.lastname: Weber
authors.affiliation: Fachbereich Chemie, Philipps-Universität Marburg , Hans-Meerwein-Straße 4, D-35043 Marburg, Germany.
authors.forename: Monika
authors.initials: M
authors.lastname: Ballmann
authors.affiliation: Fachbereich Chemie, Philipps-Universität Marburg , Hans-Meerwein-Straße 4, D-35043 Marburg, Germany.
authors.forename: Corinna
authors.initials: C
authors.lastname: Kohlmeyer
authors.affiliation: Fachbereich Chemie, Philipps-Universität Marburg , Hans-Meerwein-Straße 4, D-35043 Marburg, Germany.
authors.forename: Gerhard
authors.initials: G
authors.lastname: Hilt
mesh_terms: D000438:Alcohols / Q000737:chemistry; D000447:Aldehydes / Q000737:chemistry; D001897:Boronic Acids / Q000138:chemical synthesis / Q000737:chemistry*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D004952:Esters / Q000737:chemistry; D007495:Iridium / Q000737:chemistry; D015394:Molecular Structure; D009532:Nickel / Q000737:chemistry*; D013237:Stereoisomerism; D015032:Zinc / Q000737:chemistry
chemical_list: D000438:Alcohols; D000447:Aldehydes; D001897:Boronic Acids; D004952:Esters; D007495:Iridium; D009532:Nickel; D015032:Zinc