Cooperative Catalysis for the First Asymmetric Formal [3+2] Cycloaddition Reaction of Isocyanoacetates to α,β-Unsaturated Ketones

被引：70

作者：

Arroniz, Carlos ^{[1
,2
]}

Gil-Gonzalez, Alberto ^{[1
,2
]}

Semak, Vladislav ^{[1
,2
]}

Escolano, Carmen ^{[1
,2
]}

Bosch, Joan ^{[1
,2
]}

Amat, Mercedes ^{[1
,2
]}

机构：

[1] Univ Barcelona, Fac Pharm, Organ Chem Lab, E-08028 Barcelona, Spain

[2] Univ Barcelona, Inst Biomed IBUB, E-08028 Barcelona, Spain

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 2011卷 / 20-21期

关键词：

Silver; Organocatalysis; Ketones; Domino reactions; Asymmetric synthesis; ENANTIOSELECTIVE CONJUGATE ADDITION; MULTICOMPONENT REACTIONS; CASCADE REACTIONS; ACID; ORGANOCATALYSIS; METAL; ISOCYANOESTERS; ISOCYANIDES; GOLD;

D O I：

10.1002/ejoc.201100409

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A cooperative multicatalytic cascade sequence involving isocyanoacetates and alpha,beta-unsaturated ketones is described for the enantioselective synthesis of 2,3-dihydropyrroles. The key to promoting the multistep asymmetric reaction is the combination of cinchona alkaloid derived organocatalysts with silver nitrate. Merging both organic and metal catalytic cycles enables the formation of two C-C bonds and the generation of a stereogenic center in a single process. The study has also shown that the bifunctional role of the organocatalyst is crucial for the asymmetric version of the cycloaddition reaction.

引用

页码：3755 / 3760

页数：6

共 55 条

[1] Cooperative Organocatalysis for the Asymmetric γ Alkylation of α-Branched Enals [J].