Asymmetric aerobic oxidative NHC-catalysed synthesis of dihydropyranones utilising a system of electron transfer mediators

被引:36
作者
Axelsson, A. [1 ]
Hammarvid, E. [1 ]
Ta, L. [1 ]
Sunden, H. [1 ]
机构
[1] Chalmers Univ Technol, Chem & Chem Engn, Kemivagen 10, S-41296 Gothenburg, Sweden
基金
瑞典研究理事会;
关键词
N-HETEROCYCLIC CARBENES; ENANTIOSELECTIVE MICHAEL REACTIONS; ALPHA; BETA-UNSATURATED ALDEHYDES; MOLECULAR-OXYGEN; 1,3-DICARBONYL COMPOUNDS; WACKER PROCESS; ACYL AZOLIUMS; ANNULATION; REARRANGEMENT; ACTIVATION;
D O I
10.1039/c6cc06060a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
In the context of green chemistry, the replacement of high molecular weight stoichiometric oxidants with O-2 is most desirable but difficult. Here, we report the asymmetric aerobic oxidative synthesis of dihydropyranones. The oxidation is aided by a system of electron transfer mediators and is selective toward the homoenolate. The dihydropyranones can be isolated in high to excellent yields, with high ee (up to 95%).
引用
收藏
页码:11571 / 11574
页数:4
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