1,2-N-Migration in a Gold-Catalysed Synthesis of Functionalised Indenes by the 1,1-Carboalkoxylation of Ynamides

被引：56

作者：

Adcock, Holly V. ^{[1
]}

Langer, Thomas ^{[2
]}

Davies, Paul W. ^{[1
]}

机构：

[1] Univ Birmingham, Sch Chem, Birmingham B15 2TT, W Midlands, England

[2] AstraZeneca, Pharmaceut Dev, Macclesfield SK10 2NA, Cheshire, England

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2014年 / 20卷 / 24期

基金：

英国工程与自然科学研究理事会;

关键词：

carbenes; cycloisomerisation; gold; regioselectivity; ynamides; GOLD(I)-CATALYZED CYCLOISOMERIZATION; INTRAMOLECULAR CARBOALKOXYLATION; HOMOPROPARGYLIC AMINES; PLATINUM; CYCLIZATION; MIGRATION; ALKYNES; REARRANGEMENTS; ACTIVATION; REACTIVITY;

D O I：

10.1002/chem.201403040

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Unique alpha-hemiaminal ether gold carbene intermediates were accessed by a gold-catalysed 1,1-carboalkoxylation strategy and evolved through a highly selective 1,2-N-migration. This skeletal rearrangement gave functionalised indenes, and isotopic labelling confirmed the rare C-N bond cleavage of the ynamide moiety. The effect of substituents on the migration has been explored, and a model is proposed to rationalise the observed selectivity.

引用

页码：7262 / 7266

页数：5

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