Rh-catalyzed enantioselective diboration of simple alkenes: reaction development and substrate scope.
[Reaction: see text]. The rhodium-catalyzed reaction between bis(catecholato)diboron and simple alkenes results in the syn addition of the diboron across the alkene. The resulting 1,2-bis(boronate) is subsequently oxidized to provide the 1,2-diol. In the presence of enantiomerically enriched Quinap ligand, high enantioselection in the diboration can be achieved. The reaction is highly selective for trans- and trisubstituted alkenes and can be selective for some monosubstituted alkenes as well. The development of this reaction is described as is the substrate scope and experiments that are informative about the reaction mechanism and competing pathways.
Trudeau
Stéphane
S
Department of Chemistry, Venable and Kenan Laboratories, The University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599-3290, USA.
Morgan
Jeremy B
JB
Shrestha
Mohanish
M
Morken
James P
JP
D000475:Alkenes / Q000737:chemistry*; D001896:Boron Compounds / Q000737:chemistry*; D002384:Catalysis; D008024:Ligands; D015394:Molecular Structure; D010084:Oxidation-Reduction; D012238:Rhodium / Q000737:chemistry*; D013237:Stereoisomerism
D000475:Alkenes; D001896:Boron Compounds; D008024:Ligands; D012238:Rhodium