Synthesis of Barbaralones and Bullvalenes Made Easy by Gold Catalysis

被引：40

作者：

Ferrer, Sofia ^{[1
]}

Echavarren, Antonio M. ^{[1
,2
]}

机构：

[1] Barcelona Inst Sci & Technol, Inst Chem Res Catalonia ICIQ, Ave Paisos Catalans 16, Tarragona 43007, Spain

[2] Univ Rovira & Virgili, Dept Quim Analit & Quim Organ, C Marcelli Domingo S-N, E-43007 Tarragona, Spain

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2016年 / 55卷 / 37期

基金：

欧洲研究理事会;

关键词：

barbaralones; bullvalenes; cyclization reactions; gold; valence tautomerism; DEGENERATE COPE REARRANGEMENT; SHAPESHIFTING ORGANIC-MOLECULES; RETRO-BUCHNER REACTION; X-RAY CRYSTALLOGRAPHY; SOLID-STATE; C-13; NMR; INTRAMOLECULAR CYCLIZATION; MAGNETIC-RESONANCE; REACTION PATHWAYS; DEUTERIUM;

D O I：

10.1002/anie.201606101

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The gold(I)-catalyzed oxidative cyclization of 7-ethynyl-1,3,5-cycloheptatrienes gives 1-substituted barbaralones in a general manner, which simplifies the access to other fluxional molecules. As an example, we report the shortest syntheses of bullvalene, phenylbullvalene, and disubstituted bullvalenes, and a readily accessible route to complex cage-type structures by further gold(I)-catalyzed reactions.

引用

页码：11178 / 11182

页数：5

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