KetoABNO/NOx Cocatalytic Aerobic Oxidation of Aldehydes to Carboxylic Acids and Access to α-Chiral Carboxylic Acids via Sequential Asymmetric Hydroformylation/Oxidation

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• 作者：Kelsey C. Miles ; M. Leigh Abrams ; Clark R. Landis ; Shannon S. Stahl
• 刊名：Organic Letters
• 出版年：2016
• 出版时间：August 5, 2016
• 年：2016
• 卷：18
• 期：15
• 页码：3590-3593
• 全文大小：373K
• 年卷期：0
• ISSN：1523-7052

文摘

A method for aerobic oxidation of aldehydes to carboxylic acids has been developed using organic nitroxyl and NO_x cocatalysts. KetoABNO (9-azabicyclo[3.3.1]nonan-3-one N-oxyl) and NaNO₂ were identified as the optimal nitroxyl and NO_x 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.