Organocatalytic Asymmetric Dearomative Spirocyclization/Oxa-Michael Addition Sequence: Synthesis of Polycyclic Tetralones
Ramji Meher, Subhas Chandra Pan
Abstract
Herein, an organocatalytic asymmetric dearomative spirocyclization/oxa-Michael addition sequence with a newly designed substrate having two naphthol motifs has been developed. The reaction proceeds through in situ chiral vinylidene ortho -quinone methide (VQM) intermediate formation, dearomative spirocyclization of naphthol, and an oxa-Michael addition reaction. The densely functionalized tetralone products were formed in high yields with high diastereo- and enantioselectivities.
Topics & Concepts
ChemistryMichael reactionTetralonesSequence (biology)TetraloneSubstrate (aquarium)Combinatorial chemistryStereochemistryOrganic chemistryCatalysisBiochemistryBiologyEcologyOxidative Organic Chemistry ReactionsAxial and Atropisomeric Chirality SynthesisAlkaloids: synthesis and pharmacology