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Preparation of 6-aminocyclohepta-2,4-dien-1-one Derivatives via Tricarbonyltroponeiron
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Enantioselective Tandem Michael Addition and Cyclization Reaction Enabled by Dual Organo/Copper Catalysis: Access to
Khushboo Gupta1, Nidhi Saini1, Shweta Rohilla1
1Department of Chemistry, Indian Institute of Technology Kanpur, Kanpur, Uttar Pradesh 208 016, India.
None:
An enantioselective (3 + 3) annulation between 1,3-nitroenynes and α-cyano ketones has been developed using a cooperative organo/copper dual catalytic system. The transformation proceeds through an enantioselective Michael addition catalyzed by the synergistic effect of an organocatalyst and metal-ligand complex, followed by Lewis-acid-catalyzed annulation, furnishing pentasubstituted 4H-pyran derivatives in good yields and good to excellent enantioselectivities. Mechanistic investigations were conducted to elucidate the reaction pathway, and its practical applicability was demonstrated through a scale-up reaction and versatile post synthetic modifications.
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