Enantioselective total synthesis of furofuran lignans <i>via</i> Pd-catalyzed asymmetric allylic cycloadditon of vinylethylene carbonates with 2-nitroacrylates
Can Zhao, Ijaz Khan, Yong Jian Zhang
Abstract
Herein, a practical and efficient approach to tetrahydrofurans with three-stereocenters has been developed through Pd-catalyzed asymmetric allylic cycloaddition of vinylethylene carbonates (VECs) with 2-nitroacrylates under mild conditions. By using this asymmetric catalytic reaction as a key step, several furofuran lignans with stereodivergency have been effectively synthesized through 5- or 6-step sequences from readily available starting materials.
Topics & Concepts
Enantioselective synthesisAllylic rearrangementChemistryCatalysisCombinatorial chemistryOrganic chemistryStereochemistryPlant-derived Lignans Synthesis and BioactivitySynthesis of Indole DerivativesCatalytic Alkyne Reactions