Synthesis of Functionalized Cyclobutenes and Spirocycles <i>via</i> Asymmetric P(III)/P(V) Redox Catalysis
Charlotte Lorton, Antoine Roblin, Pascal Retailleau, Arnaud Voituriez
Abstract
Abstract An enantioselective phosphine‐catalyzed transformation has been developed for the synthesis of chiral cyclobutene triesters and fluorinated spirocyclic compounds. The strategy involved a P(III)/P(V) redox cycling process, via in situ reduction of phosphine oxide with phenylsilane. This catalytic methodology has enabled the enantioselective synthesis of functionalized cyclobutenes (24 examples, up to 94% ee). On the occasion of the extension of this study to α‐ketoester indenone substrates, a surprising reactivity has been discovered for the synthesis of spiro‐indenone products. magnified image
Topics & Concepts
Enantioselective synthesisChemistryCyclobutenePhosphineRedoxCatalysisCombinatorial chemistryPhosphine oxideReactivity (psychology)PhenylsilaneOrganic chemistryRing (chemistry)Alternative medicineMedicinePathologyAsymmetric Hydrogenation and CatalysisAsymmetric Synthesis and CatalysisChemical Synthesis and Analysis