Palladium catalysts for aerobic oxidative kinetic resolution of secondary alcohols based on mechanistic insight.
The oxidative kinetic resolution of secondary alcohols has been accomplished using 1:1 complexes of PdCl(2) and N-heterocyclic carbenes. In these reactions, both achiral and chiral carbene ligands are used in conjunction with the chiral base (-)-sparteine. A general synthesis of 1:1 PdCl(2)-carbene complexes has been developed and is amenable to a wide range of carbene ligands. The potential of these complexes in aerobic oxidations is highlighted by the use of a chiral Pd(II) complex and the chiral base (-)-sparteine to enhance the kinetic resolution of a racemic alcohol. [reaction--see text]
Jensen
David R
DR
Department of Chemistry, University of Utah, Salt Lake City, UT 84112, USA.
Sigman
Matthew S
MS
D000438:Alcohols / Q000737:chemistry*; D002384:Catalysis; D007700:Kinetics; D015394:Molecular Structure; D010100:Oxygen / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*
D000438:Alcohols; D010165:Palladium; C008756:palladium chloride; D010100:Oxygen