142405-11-6Relevant articles and documents
Catalytic Hydroetherification of Unactivated Alkenes Enabled by Proton-Coupled Electron Transfer
Knowles, Robert R.,Metrano, Anthony J.,Tsuchiya, Yuto,Tsui, Elaine
, p. 11845 - 11849 (2020)
We report a catalytic, light-driven method for the intramolecular hydroetherification of unactivated alkenols to furnish cyclic ether products. These reactions occur under visible-light irradiation in the presence of an IrIII-based photoredox catalyst, a Br?nsted base catalyst, and a hydrogen-atom transfer (HAT) co-catalyst. Reactive alkoxy radicals are proposed as key intermediates, generated by direct homolytic activation of alcohol O?H bonds through a proton-coupled electron-transfer mechanism. This method exhibits a broad substrate scope and high functional-group tolerance, and it accommodates a diverse range of alkene substitution patterns. Results demonstrating the extension of this catalytic system to carboetherification reactions are also presented.
N-Alkenyl Nitrone Dipolar Cycloaddition Routes to Piperidines and Indolizidines. Part 3. Approach to the Gephyrotoxin Ring System
Holmes, Andrew B.,Hughes, Andrew B.,Smith, Adrian L.,Williams, Simon F.
, p. 1089 - 1100 (2007/10/02)
Intramolecular dipolar cycloaddition studies on the N-alkenyl nitrones 16, 17, 36 and 45 are reported.The regio- and stereo-chemistry of the product bicyclic isoxazolidines (precursors to ring B of gephyrotoxin 1) are sensitive to the nature and geometry
