title: Palladium-catalyzed enantioselective diboration of prochiral allenes.
abstract: Pd-catalyzed diboration of prochiral allenes occurs exclusively at the internal position and is remarkably accelerated in the presence of Lewis basic ligand structures. On the basis of preliminary observations, a chiral ligand was employed, and the enantiomeric excess of a variety of diboration products was found to be in the range of 86-92% ee. The chiral diboron reaction products should be useful in organic synthesis, and preliminary experiments suggest that they may participate in allylation reactions with a high level of chirality transfer.
authors.affiliation: Department of Chemistry, Venable and Kenan Laboratories, The University of North Carolina, Chapel Hill, North Carolina 27599-3290, USA.
authors.forename: Nicholas F
authors.initials: NF
authors.lastname: Pelz
authors.forename: Angela R
authors.initials: AR
authors.lastname: Woodward
authors.forename: Heather E
authors.initials: HE
authors.lastname: Burks
authors.forename: Joshua D
authors.initials: JD
authors.lastname: Sieber
authors.forename: James P
authors.initials: JP
authors.lastname: Morken
mesh_terms: D000466:Alkadienes / Q000737:chemistry*; D001896:Boron Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D009943:Organophosphorus Compounds / Q000737:chemistry; D010165:Palladium / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000466:Alkadienes; D001896:Boron Compounds; D009943:Organophosphorus Compounds; C434331:phosphoramidite; C025947:propadiene; D010165:Palladium