title: Novel Chiral Bifunctional L-Thiazoline-Thiourea Derivatives: Design and Application in Enantioselective Michael Reactions.
abstract: Several novel chiral bifunctional L-thiazoline-thiourea derivatives were easily synthesized from commercially available L-cysteine in high yield. These catalysts were subsequently applied to the enantioselective Michael addition of acetylacetone to β-nitrostyrenes. The products with S configuration were obtained in 98% enantiomeric excess (ee) when the L-thiazoline-thiourea derivatives were used. A plausible transition state model is proposed to explain the observed enantioselectivities.
authors.affiliation: Department of Organic Chemistry, College of Chemistry, Jilin University, Changchun, China.
authors.forename: Qi
authors.initials: Q
authors.lastname: Lai
authors.affiliation: Department of Organic Chemistry, College of Chemistry, Jilin University, Changchun, China.
authors.forename: Yang
authors.initials: Y
authors.lastname: Li
authors.affiliation: Department of Organic Chemistry, College of Chemistry, Jilin University, Changchun, China.
authors.forename: Zhiyong
authors.initials: Z
authors.lastname: Gong
authors.affiliation: Department of Organic Chemistry, College of Chemistry, Jilin University, Changchun, China.
authors.forename: Qingwen
authors.initials: Q
authors.lastname: Liu
authors.affiliation: Department of Organic Chemistry, College of Chemistry, Jilin University, Changchun, China.
authors.forename: Chiyu
authors.initials: C
authors.lastname: Wei
authors.affiliation: Department of Organic Chemistry, College of Chemistry, Jilin University, Changchun, China.
authors.forename: Zhiguang
authors.initials: Z
authors.lastname: Song
mesh_terms: D009682:Magnetic Resonance Spectroscopy; D021241:Spectrometry, Mass, Electrospray Ionization; D013237:Stereoisomerism; D013844:Thiazoles / Q000737:chemistry*; D013890:Thiourea / Q000737:chemistry*
chemical_list: D013844:Thiazoles; D013890:Thiourea
keywords: asymmetric Michael addition; chiral catalyst; thiazoline; thiourea