Ruthenium catalyzed one-pot synthesis of dihydro-pyrrol-2-one derivatives from α,β-unsaturated imines, carbon monoxide and ethylene

被引：41

作者：

Berger, D ^{[1
]}

Imhof, W ^{[1
]}

机构：

[1] Univ Jena, Inst Anorgan & Analyt Chem, D-07743 Jena, Germany

来源：

TETRAHEDRON | 2000年 / 56卷 / 14期

关键词：

catalysis; pyrrolones; isoindoles; C-C bond formation; X-ray structural analysis;

D O I：

10.1016/S0040-4020(00)00118-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The use of Ru-3(CO)(12) as a precatalyst induces a catalytic C-C coupling reaction of alpha,beta-unsaturated imines with CO to yield imines with an aldehyde function in beta-position with respect to the C-N double bond. An intramolecular cyclization reaction takes place via the nucleophilic attack of the imine nitrogen towards the carbonyl carbon atom building up a pyrrol-2-one system. A second ruthenium catalyzed C-C coupling reaction leads to the formal insertion of one molecule of ethylene into a C-H bond of the pyrrol-2-one in ortho position with respect to the keto group. By this selective reaction cascade imines derived from cinnamaldehyde or crotonic aldehyde, respectively, produce 1,3-dihydro-pyrrol-2-one derivatives. The analogous reaction starting from beta-naphthylaldimines yields 9b-ethyl-4-propionyl-2,9b-dihydro-benzo[e]isoindol- 1-one derivatives as a new class of heterocyclic compounds. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：2015 / 2023

页数：9

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