FeBr3-catalyzed Fully Intermolecular [2+2+2] Cycloaddition of Alkenes

被引：1

作者：

Tomifuji, Rei ^{[1
]}

Murano, Shunpei ^{[1
]}

Kurahashi, Takuya ^{[1
]}

Matsubara, Seijiro ^{[1
]}

机构：

[1] Kyoto Univ, Grad Sch Engn, Dept Mat Chem, Kyoto 6158510, Japan

来源：

CHEMISTRY LETTERS | 2021年 / 50卷 / 12期

关键词：

Cycloaddition; Lewis acid; Iron; DIELS-ALDER REACTION; POLYMERIZATION; HYDROGENATION; ALLYLSILANES; ION;

D O I：

10.1246/cl.210552

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A methodology for the synthesis of cyclohexane scaffolds has been developed. The unprecedented fully intermolecular [2+2+2] cycloaddition reaction of three alkenes was catalyzed by an iron(III)-based Lewis acid to give multi-substituted cyclohexane products in a diastereoselective manner. The ionic species [FeBr2](+)[FeBr4](-) generated via disproportionation of FeBr3 is crucial for this catalysis: the strong Lewis acidity of [FeBr2](+) facilitates the addition reaction of alkenes, and [FeBr4](-) controls the reaction path suppressing the undesired polymerization reaction by forming a dormant-like intermediate. This protocol offers a new synthetic way to obtain cyclohexane cycloadduct.

引用

页码：2018 / 2021

页数：4

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