title: Asymmetric Mannich synthesis of α-amino esters by anion-binding catalysis.
abstract: We report a scalable, one-pot Mannich route to enantioenriched α-amino esters by direct reaction of α-chloroglycine ester as a practical imino ester surrogate. The reaction is promoted by a chiral aminothiourea, which is proposed to operate cooperatively by generating an iminium ion by chloride abstraction and an enolate by deprotonation, followed by highly stereoselective C-C bond formation between both reactive intermediates associated non-covalently within the catalyst framework.
authors.affiliation: Department of Chemistry & Chemical Biology, Harvard University , Cambridge, Massachusetts 02138, United States.
authors.forename: Masayuki
authors.initials: M
authors.lastname: Wasa
authors.forename: Richard Y
authors.initials: RY
authors.lastname: Liu
authors.forename: Stéphane P
authors.initials: SP
authors.lastname: Roche
authors.forename: Eric N
authors.initials: EN
authors.lastname: Jacobsen
mesh_terms: D000586:Amination; D000588:Amines / Q000138:chemical synthesis* / Q000737:chemistry; D000838:Anions / Q000737:chemistry*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D004952:Esters / Q000138:chemical synthesis* / Q000737:chemistry; D005998:Glycine / Q000031:analogs & derivatives; D054879:Halogenation; D013890:Thiourea / Q000737:chemistry
chemical_list: D000588:Amines; D000838:Anions; D004952:Esters; D013890:Thiourea; D005998:Glycine