Chemoselective and Diastereoconvergent Cu(II)-Catalyzed Aerobic Endoperoxidation of Polycarbonyls

被引：11

作者：

Giarrusso, James ^{[1
]}

Do, Dung T. ^{[1
]}

Johnson, Jeffrey S. ^{[1
]}

机构：

[1] Univ North Carolina Chapel Hill, Dept Chem, Chapel Hill, NC 27599 USA

来源：

ORGANIC LETTERS | 2017年 / 19卷 / 12期

基金：

美国国家科学基金会;

关键词：

ALPHA-KETO ESTERS; ORGANIC PEROXIDES; BETA-KETOESTERS; OXYGEN; HYDROGENATION; ARTEMISININ; OXIDATION; PRODUCTS; IONS;

D O I：

10.1021/acs.orglett.7b01225

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The diastereoconvergent synthesis of spirocyclic endoperoxides using a Meldrum's acid scaffold has been accomplished by employing readily available feedstock Chemicals. Site selective C-H oxidation of the bis(beta-dicarbonyl) substrates was performed using, elemental oxygen as the stoichiometric oxidant and a commercial Cu(II) catalyst. Sequential hydrogenolysis and ionic reduction of these-endoperoxides provided fully substituted tetrahydrofurans in high-yields and diastereoselectivity.

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收藏

页码：3107 / 3110

页数：4

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