Thilmany Pierre, Guarnieri-Ibáñez Alejandro, Jacob Clément, Lacour Jérôme, Evano Gwilherm
Laboratoire de Chimie Organique, Service de Chimie et PhysicoChimie Organiques, Université libre de Bruxelles (ULB), Avenue F. D. Roosevelt 50, CP160/06, 1050 Brussels, Belgium.
Department of Organic Chemistry, University of Geneva, Quai Ernest Ansermet 30, 1211 Geneva 4, Switzerland.
ACS Org Inorg Au. 2021 Oct 14;2(1):53-58. doi: 10.1021/acsorginorgau.1c00021. eCollection 2022 Feb 2.
An original and straightforward entry to polysubstituted indenes from readily available ynamides is reported. Upon reaction with a -heterocyclic carbene-gold complex under mild conditions, activated keteniminium ions are generated whose unique electrophilicity triggers a [1,5]-hydride shift and a subsequent cyclization. The presence of an endocyclic enamide in the densely functionalized resulting indenes was shown to be especially useful and versatile, offering a range of opportunities for their further postfunctionalization.
报道了一种从容易获得的烯酰胺出发合成多取代茚的新颖且直接的方法。在温和条件下与α-杂环卡宾-金络合物反应时,会生成活化的烯酮亚胺离子,其独特的亲电性引发[1,5]-氢迁移和随后的环化反应。结果表明,在功能密集的所得茚中存在内酰胺环特别有用且用途广泛,为其进一步的后期功能化提供了一系列机会。