Intramolecular Activation of Enones by Electrophilic Phosphinidene Complexes to Construct 2-Phosphafurans
Li Hong, Rongqiang Tian, Zheng Duan
Abstract
Herein, we report a facile and highly atom-economic approach to 2-phosphafurans by using simple 2-chloroethylphosphine and acetylenic ketones. The key step of this protocol utilizes the Lewis acidity of electrophilic phosphinidenes to induce an intramolecular cyclization with enones. Dearomative hetero-Diels-Alder reactions of 2-phosphafurans provide two series of bicyclic phosphacycles. This rare synthetic application of Lewis acidity of electrophilic phosphinidene complexes represents a new frontier of phosphinidene chemistry.
Topics & Concepts
PhosphinideneChemistryElectrophileIntramolecular forceLewis acids and basesBicyclic moleculeMedicinal chemistryStereochemistryOrganic chemistryCatalysisOrganophosphorus compounds synthesisAsymmetric Synthesis and CatalysisSynthetic Organic Chemistry Methods