Oxyphosphonium Enolate Equilibria in a (4+1)‐Cycloaddition Approach toward Quaternary C3‐Spirooxindole Assembly
Eva M. Gulotty, Kevin X. Rodriguez, Erin E. Parker, Brandon L. Ashfeld
Abstract
An efficient and convergent (4+1)-cycloaddition strategy toward the construction of spirooxindole benzofurans that involves the intermediacy of an isatin-derived oxyphosphonium enolate is presented. Mechanistic investigations employing in situ NMR analysis of the reaction mixture revealed a correlation between phosphonium enolate structure and product distribution that was heavily influenced by the solvent and reaction temperature.
Topics & Concepts
CycloadditionPhosphoniumIsatinProduct distributionChemistrySolventReaction conditionsComputational chemistryOrganic chemistryCombinatorial chemistryCatalysisAsymmetric Synthesis and CatalysisCarbohydrate Chemistry and SynthesisSynthetic Organic Chemistry Methods