Catalytic Asymmetric Michael Reaction of 5H‐Oxazol‐4‐Ones with α, β‐Unsaturated Acyl Imidazoles. Issue 48 (14th October 2015)

• Record Type: Journal Article
• Authors: Zhang, Bangzhi; Han, Fengxia; Wang, Linqing; Li, Dan; Yang, Dongxu; Yang, Xiaoli; Yang, Junxian; Li, Xiaofang; Zhao, Depeng; Wang, Rui
• Is Part Of: Chemistry. Volume 21:Issue 48(2015)
• Page Start: 17234
• Page End: 17238
• Publication Date: 2015-10-14
• Subjects: asymmetric synthesis -- heterocycles -- ligand design -- Michael addition -- zinc; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201503105
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: The asymmetric Michael reaction between 5 H ‐oxazol‐4‐ones and α, β‐unsaturated acyl imidazoles is reported. A novel 2‐benzo[ b ]thiophenyl‐modified chiral ProPhenol species is synthesized and used as a ligand, leading to good enantioselectivities in this asymmetric conjugate addition reaction. Furthermore, the introduction of phenol additives as achiral co‐ligands is found to improve the reaction's chemical yields, diastereoselectivities, and enantioselectivities. Abstract : Is that your phenol answer? The asymmetric Michael reaction between 5 H ‐oxazol‐4‐ones and α, β‐unsaturated acyl imidazoles is realized by utilizing a dinuclear zinc complex catalyst. The introduction of phenol additive as an achiral co‐ligand is found to improve the reaction's chemical yields, diastereoselectivities, and enantioselectivities.