Iron(III)-Catalyzed (4 + 2)-Cycloannulation of 2-Hydroxy Ketoxime Ethers with Indol-2-ylamides: Synthesis of Indole-Fused 2-Piperidinones,The Journal of Organic Chemistry

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Iron(III)-Catalyzed (4 + 2)-Cycloannulation of 2-Hydroxy Ketoxime Ethers with Indol-2-ylamides: Synthesis of Indole-Fused 2-Piperidinones
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2019-03-27 00:00:00 , DOI: 10.1021/acs.joc.9b00261
Marcel Schlegel ₁ , Christoph Schneider ₁

Affiliation

A highly regio- and diastereoselective (4 + 2)-cycloannulation process of indanone-derived 2-hydroxy ketoxime ethers with 1,4-bisnucleophilic indol-2-ylamides has been developed. In the presence of 5 mol % FeCl₃, densely functionalized 2-piperidinones containing two new σ-bonds and two vicinal quaternary stereogenic centers were formed under mild reaction conditions in a one-pot operation. Moreover, most of the products directly precipitated out of the solution and were isolated by simple filtration without purification by column chromatography.

中文翻译：

铁（III）催化的吲哚-2-基酰胺与2-羟基酮肟醚的（4 + 2）环环化反应：吲哚融合的2-哌啶酮的合成

已开发出由茚满酮衍生的2-羟基酮肟醚与1,4-双亲核吲哚-2-基酰胺的高度区域选择性和非对映选择性（4 + 2）-环环化工艺。在5 mol％FeCl ₃的存在下，在一锅操作中，在温和的反应条件下，形成了含有两个新的σ键和两个相邻的季铵立体构型中心的稠密官能化的2-哌啶酮。而且，大多数产物直接从溶液中沉淀出来，并通过简单过滤分离而无需通过柱色谱法纯化。

更新日期：2019-03-27

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