Organocatalytic Asymmetric Dearomatization Reaction for the Construction of Axially Chiral Urazole Embedded Naphthalenones
Chandrakanta Parida, Siddharth K. Dave, Kousik Das, Subhas Chandra Pan
Abstract
Abstract Herein we disclose a catalytic asymmetric dearomatization reaction of β‐ naphthols with 4‐aryl‐1,2,4‐triazole‐3,5‐diones. A chiral phosphoric acid with spiro motif was found to be effective for this reaction. The chiral urazole embedded naphthalenones having both axial and central chirality were obtained in good to high yields (70–85%) with high diastereo‐ and enantioselectivities (>20:1, 8–96% ees), having C−N rotational energy barrier 31.54 K.Cal.mol −1 and t 1/2 25 °C=589.8 years. The scope of the reaction was broad and few applications including a bromo‐amination reaction have been demonstrated. magnified image
Topics & Concepts
ChemistryCatalysisAminationArylAxial chiralityChirality (physics)Enantioselective synthesisCombinatorial chemistryOrganic chemistryMedicinal chemistryStereochemistryChiral symmetryPhysicsNambu–Jona-Lasinio modelAlkylQuantum mechanicsQuarkAxial and Atropisomeric Chirality SynthesisAsymmetric Synthesis and CatalysisMolecular spectroscopy and chirality