One-pot synthesis of tetrasubstituted 2-aminofurans via Au(i)-catalyzed cascade reaction of ynamides with propargylic alcohols
- 22 October 2021
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Organic & Biomolecular Chemistry
- Vol. 19 (43), 9396-9400
- https://doi.org/10.1039/d1ob01910d
Abstract
One-pot synthesis of fully substituted 2-aminofurans via a Au(I)-catalyzed cascade reaction of ynamides and propargylic alcohol was realized. Hydroalkoxylation of ynamide with propargylic alcohol, Saucy–Marbet rearrangement, and cyclization of the resultant 3,4-dienamide sequentially proceeds in a one-pot reaction under highly mild conditions to give fully substituted 2-aminofurans.Funding Information
- Japan Society for the Promotion of Science (Grant-in Aid for Scientific Research (B) / 20H0336, Grant-in Aid for Scientific Research (C) / 20K0696)
- Nagase Science Technology Foundation
- Akiyama Life Science Foundation
This publication has 34 references indexed in Scilit:
- Regio‐ and Stereoselective Synthesis of Tri‐ and Tetrasubstituted Enamides via Palladium‐Catalyzed Silaboration of YnamidesAdvanced Synthesis & Catalysis, 2013
- Total Synthesis of (−)-Herbindoles A, B, and C via Transition-Metal-Catalyzed Intramolecular [2 + 2 + 2] Cyclization between Ynamide and DiynesOrganic Letters, 2012
- Gosteli−Claisen Rearrangement of Propargyl Vinyl Ethers: Cascading Molecular RearrangementsOrganic Letters, 2011
- Ynamides: A Modern Functional Group for the New MillenniumChemical Reviews, 2010
- Ynamides: Versatile Tools in Organic SynthesisAngewandte Chemie, 2010
- Gold-catalyzed cycloisomerization of alk-4-yn-1-onesOrganic & Biomolecular Chemistry, 2009
- Nickel-Catalyzed Highly Regioselective Multicomponent Coupling of Ynamides, Aldehydes, and Silane: A New Access to Functionalized EnamidesOrganic Letters, 2008
- Syntheses of polysubstituted furans: recent developmentsOrganic & Biomolecular Chemistry, 2006
- Über eine neuartige Synthese von β‐Ketoallenen durch Reaktion von tertiären Acetylencarbinolen mit Vinyläthern eine ergiebige methode zur darstellung des Pseudojonons und verwandter verbindungenHelvetica Chimica Acta, 1967
- Zur Kenntnis der Pseudojononsynthese nach Kimel & SaxHelvetica Chimica Acta, 1958