title: Enantioselective Allylic C-H Oxidation of Terminal Olefins to Isochromans by Palladium(II)/Chiral Sulfoxide Catalysis.
abstract: The enantioselective synthesis of isochroman motifs has been accomplished by palladium(II)-catalyzed allylic C-H oxidation from terminal olefin precursors. Critical to the success of this goal was the development and utilization of a novel chiral aryl sulfoxide-oxazoline (ArSOX) ligand. The allylic C-H oxidation reaction proceeds with the broadest scope and highest levels of asymmetric induction reported to date (avg. 92 % ee, 13 examples with greater than 90 % ee).
authors.affiliation: Roger Adams Laboratory, Department of Chemistry, University of Illinois at Urbana-Champaign, Urbana, IL, 61801, USA.
authors.forename: Stephen E
authors.initials: SE
authors.lastname: Ammann
authors.affiliation: Roger Adams Laboratory, Department of Chemistry, University of Illinois at Urbana-Champaign, Urbana, IL, 61801, USA.
authors.forename: Wei
authors.initials: W
authors.lastname: Liu
authors.affiliation: Roger Adams Laboratory, Department of Chemistry, University of Illinois at Urbana-Champaign, Urbana, IL, 61801, USA. mcwhite7@illinois.edu.
authors.forename: M Christina
authors.initials: MC
authors.lastname: White
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D000498:Allyl Compounds / Q000737:chemistry*; D002384:Catalysis; D002839:Chromans / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism; D013454:Sulfoxides / Q000737:chemistry*
chemical_list: D000475:Alkenes; D000498:Allyl Compounds; D002839:Chromans; D013454:Sulfoxides; D010165:Palladium
keywords: C−H activation; S ligands; asymmetric catalysis; oxidation; palladium