title: KetoABNO/NOx Cocatalytic Aerobic Oxidation of Aldehydes to Carboxylic Acids and Access to α-Chiral Carboxylic Acids via Sequential Asymmetric Hydroformylation/Oxidation.
abstract: A method for aerobic oxidation of aldehydes to carboxylic acids has been developed using organic nitroxyl and NOx cocatalysts. KetoABNO (9-azabicyclo[3.3.1]nonan-3-one N-oxyl) and NaNO2 were identified as the optimal nitroxyl and NOx sources, respectively. The mildness of the reaction conditions enables sequential asymmetric hydroformylation of alkenes/aerobic aldehyde oxidation to access α-chiral carboxylic acids without racemization. The scope, utility, and limitations of the oxidation method are further evaluated with a series of achiral aldehydes bearing diverse functional groups.
authors.affiliation: Department of Chemistry, University of Wisconsin-Madison , 1101 University Avenue, Madison, Wisconsin 53706, United States.
authors.forename: Kelsey C
authors.initials: KC
authors.lastname: Miles
authors.affiliation: Department of Chemistry, University of Wisconsin-Madison , 1101 University Avenue, Madison, Wisconsin 53706, United States.
authors.forename: M Leigh
authors.initials: ML
authors.lastname: Abrams
authors.affiliation: Department of Chemistry, University of Wisconsin-Madison , 1101 University Avenue, Madison, Wisconsin 53706, United States.
authors.forename: Clark R
authors.initials: CR
authors.lastname: Landis
authors.affiliation: Department of Chemistry, University of Wisconsin-Madison , 1101 University Avenue, Madison, Wisconsin 53706, United States.
authors.forename: Shannon S
authors.initials: SS
authors.lastname: Stahl
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D002264:Carboxylic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D006574:Heterocyclic Compounds, 2-Ring / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D012977:Sodium Nitrite / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D002264:Carboxylic Acids; D006574:Heterocyclic Compounds, 2-Ring; D012977:Sodium Nitrite