title: Catalyst-controlled Wacker-type oxidation of homoallylic alcohols in the absence of protecting groups.
abstract: Homoallylic alcohols are oxidized to β-hydroxy ketones using a TBHP-mediated Pd-catalyzed Wacker-type oxidation. The use of a bidentate ligand, quinoline-2-oxazoline (Quinox), and TBHP((aq)) as the terminal oxidant provides good yields of the desired products with reaction times significantly reduced as compared to the Tsuji-Wacker oxidation. Additionally, bis- and tris-homoallylic alcohols are oxidized to provide cyclic peroxyketals, presumably via nucleophilic attack of the methyl ketone product.
authors: University of Utah, Department of Chemistry, 315 S. 1400 E, Salt Lake City, Utah 84112, USA.
authors: Jessica R
authors: JR
authors: McCombs
authors: Brian W
authors: BW
authors: Michel
authors: Matthew S
authors: MS
authors: Sigman
mesh_terms: D002384:Catalysis; D010084:Oxidation-Reduction; D020005:Propanols / Q000737:chemistry*; D013379:Substrate Specificity
chemical_list: D020005:Propanols; C006463:allyl alcohol