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
收藏
页码：7262 / 7266
页数：5
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