Organocatalytic Regiodivergent C-C Bond Cleavage of Cyclopropenones: A Highly Efficient Cascade Approach to Enantiopure Heterocyclic Frameworks

被引：27

作者：

Cao, Jian ^{[1
]}

Fang, Ran ^{[1
]}

Liu, Jin-Yu ^{[1
]}

Lu, Hong ^{[1
]}

Luo, Yong-Chun ^{[1
]}

Xu, Peng-Fei ^{[1
]}

机构：

[1] Lanzhou Univ, State Key Lab Appl Organ Chem, Coll Chem & Chem Engn, Lanzhou 730000, Peoples R China

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2018年 / 24卷 / 71期

关键词：

density functional calculations; heterocycles; strain release; regioselectivity; FORMAL 3+2 CYCLOADDITION; CLICK CHEMISTRY; METAL-COMPLEXES; STRAIN-RELEASE; ACTIVATION; INSERTION; DIPHENYLCYCLOPROPENONE; FUNCTIONALIZATION; SUBSTITUTION; ARENES;

D O I：

10.1002/chem.201803861

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Here a highly efficient cascade approach is reported that combines a cycloaddition reaction with a regioselective strain-release process to afford diverse heterocyclic frameworks through bifunctional catalysis. The cooperation of hydrogen-bonding network activation and a regiodivergent strain-assisted effect is the key to promoting this complex chemical transformation, leading to the generation of two different ring systems in high yields with excellent stereoselectivities. The reaction proceeded by a mechanism involving a "spring-loaded" intermediate with switchable C-C bond cleavages achieved by controllable ring-strain release. This reaction was also amenable to gram scale synthesis with only 0.1 mol % catalyst loading.

引用

页码：18863 / 18867

页数：5

共 85 条

[1] Synthesis and Molecular Structure of β-Phosphinoyl Carboxamides: An Unexpected Case of Chiral Discrimination of Hydrogen-Bonded Dimers in the Solid State [J].