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

被引：25

作者：

Miles, Kelsey C. ^{[1
]}

Abrams, M. Leigh ^{[1
]}

Landis, Clark R. ^{[1
]}

Stahl, Shannon S. ^{[1
]}

机构：

[1] Univ Wisconsin, Dept Chem, 1101 Univ Ave, Madison, WI 53706 USA

来源：

ORGANIC LETTERS | 2016年 / 18卷 / 15期

基金：

美国国家科学基金会;

关键词：

TRANSITION-METAL-FREE; ALCOHOL OXIDATION; ENANTIOSELECTIVE HYDROFORMYLATION; HIGHLY EFFICIENT; MOLECULAR-OXYGEN; CATALYST; TEMPO; SYSTEM; COPPER/TEMPO; KETONES;

D O I：

10.1021/acs.orglett.6b01598

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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 alpha-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.

引用

页码：3590 / 3593

页数：4

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