Reactions of Donor Acceptor Cyclopropanes with Naphthoquinones: Redox and Lewis Acid Catalysis Working in Concert

被引：75

作者：

Luecht, Alexander ^{[1
]}

Patalag, Lukas J. ^{[1
]}

Augustin, Andre U. ^{[1
]}

Jones, Peter G. ^{[2
]}

Werz, Daniel B. ^{[1
]}

机构：

[1] Tech Univ Carolo Wilhelmina Braunschweig, Inst Organ Chem, Hagenring 30, D-38106 Braunschweig, Germany

[2] Tech Univ Carolo Wilhelmina Braunschweig, Inst Anorgan & Analyt Chem, Hagenring 30, D-38106 Braunschweig, Germany

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2017年 / 56卷 / 35期

基金：

欧洲研究理事会;

关键词：

annulation; cyclopropanes; donor-acceptor systems; naphthoquinone; tin; PARA-QUINONE METHIDES; ENOL SILYL ETHERS; CYCLOADDITION REACTIONS; 3+2 ANNULATION; SUBSTITUTED CYCLOPROPANES; CONSTRUCTION; 1,1-DIESTERS; DERIVATIVES; STRATEGY; ION;

D O I：

10.1002/anie.201703732

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Reactions of 2-arylcyclopropane dicarboxylates with naphthoquinones are reported. The key feature was the use of catalytic amounts of SnCl2, which acts as both an electron donor and a Lewis acid. By an in situ umpolung of naphthoquinone the formerly electrophilic species is converted into a nucleophile that is able to trigger the ring-opening of the three-membered ring with formation of a new C-C bond. Treatment of these products with base under oxidative condhions resulted through loss of methyl formate in cyclopenuumulated products with fully conjugated pi Systems exhibiting intensive absorptions in the visible range.

引用

页码：10587 / 10591

页数：5

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