Publication Details:
Title: Gold-catalyzed cyclization and cycloisomerization of yne-tethered ynamide: the significance of a masked enol-equivalent of an amide
Author(s) | Sanatan Nayak, B Prabagar, Akhila K Sahoo : Organic & biomolecular chemistry, 2016, 14 (3), 803-807 (Invited Prospective). |
---|---|
Journal Name | Organic & biomolecular chemistry |
journal image URL | http://chemistry.uohyd.ac.in/~aks/wp-content/uploads/sanatanobccover.png |
More Details:
This perspective briefly describes the conceptual manifestation of a Brønsted acid promoted Au-catalyzed cyclization of yne-tethered ynamides for the construction of novel N-heterocycles. A hetero-atom assisted intramolecular 6-endo-dig cyclization of a transient ketene N,O-acetal (a masked enol-ether of an amide), generated from an ambivalent ynamide through the attack of p-TsOH, with a Au-activated yne-motif creates dihydropyridinones and benzo[f]dihydroisoquinolones. The Au(I)-catalyzed cycloisomerization of an alkyne-tethered ketene N,N-acetal to manufacture unusual cyclobutene-fused azepine scaffolds is also highlighted.
https://pubs.rsc.org/en/content/articlelanding/2016/ob/c5ob02262b#!divAbstract