Stereoselective Synthesis of Dihydrocoumarins via [1,2]-Phospha-Brook Rearrangement in Three-Component Coupling Reaction of α-Ketoesters, <i>o</i>-Quinone Methides, and Dialkyl Phosphites
Ravneet Kaur, Dipak Singh, Ravi P. Singh
Abstract
A highly regio- and diastereoselective approach for the synthesis of phosphate substituted dihydrocoumarins via Brønsted base catalyzed [1,2]-phospha-Brook rearrangement is reported. The two-step, one-pot Michael addition of α-phosphonyloxy enolates proceeds by coupling of dialkyl phosphite and α-ketoesters to o-quinone methides, followed by an intramolecular cyclization, providing 3,4-dihydrocoumarin frameworks.
Topics & Concepts
ChemistryIntramolecular forceStereoselectivityQuinoneComponent (thermodynamics)Coupling (piping)Base (topology)Medicinal chemistryStereochemistryOrganic chemistryCatalysisMathematical analysisPhysicsEngineeringThermodynamicsMechanical engineeringMathematicsSynthesis of Indole DerivativesSynthesis of Organic CompoundsMulticomponent Synthesis of Heterocycles