A Facile Approach to Optically Active Hydroquinoline‐2‐carboxylates by a One‐Pot Asymmetric Michael/Transamination/Cyclization Process. Issue 9 (25th January 2016)

• Record Type: Journal Article
• Authors: Rong, Chao; Pan, Hongjie; Liu, Mao; Tian, Hua; Shi, Yian
• Is Part Of: Chemistry. Volume 22:Issue 9(2016)
• Page Start: 2887
• Page End: 2891
• Publication Date: 2016-01-25
• Subjects: cyclization -- Michael addition -- organocatalysis -- transamination; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201503327
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: An efficient one‐pot synthesis of optically active hydroquinoline‐2‐carboxylates from 1, 3‐cyclohexanediones, β, γ‐unsaturated α‐keto ester, and benzylamine in the presence of a chiral base catalyst and 1, 8‐diazabicyclo[5.4.0]undec‐7‐ene (DBU) with good diastereoselectivity and high enantioselectivity is described. The reaction proceeds by a sequential asymmetric Michael/transamination/cyclization process. Abstract : Three in one process : An efficient one‐pot synthesis of optically active hydroquinoline‐2‐carboxylates has been developed from 1, 3‐cyclohexanediones using a chiral base. The reaction proceeds by a sequential asymmetric Michael/transamination/cyclization process, giving products with high enantioselectivity and good diastereoselectivity (see scheme).