title: Highly diastereoselective and enantioselective Michael addition of 5H-oxazol-4-ones to α,β-unsaturated ketones catalyzed by a new bifunctional organocatalyst with broad substrate scope and applicability.
abstract: A new thiourea-tertiary amine bifunctional catalyst derived from L-tert-leucine was developed and provides excellent stereocontrol in a novel and direct Michael addition of 5H-oxazol-4-ones to α,β-unsaturated ketones with much broad substrate scope. The conjugate addition products with chiral vicinal quaternary and tertiary stereocenters can be easily transformed to structurally interesting compounds or building blocks.
authors.affiliation: Engineering Research Centre of Pharmaceutical Process Chemistry, Ministry of Education, School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, China.
authors.forename: Huicai
authors.initials: H
authors.lastname: Huang
authors.forename: Kailong
authors.initials: K
authors.lastname: Zhu
authors.forename: Wenbin
authors.initials: W
authors.lastname: Wu
authors.forename: Zhichao
authors.initials: Z
authors.lastname: Jin
authors.forename: Jinxing
authors.initials: J
authors.lastname: Ye
mesh_terms: D000588:Amines / Q000737:chemistry; D002384:Catalysis; D007659:Ketones / Q000737:chemistry*; D007930:Leucine / Q000737:chemistry; D010081:Oxazolone / Q000737:chemistry*; D013237:Stereoisomerism; D013890:Thiourea / Q000737:chemistry
chemical_list: D000588:Amines; D007659:Ketones; D010081:Oxazolone; D007930:Leucine; D013890:Thiourea