title: Highly stereoselective, cobalt(III)-directed Mannich additions in water yielding α-methylamino acid products.
abstract: Highly stereoselective and rapid (<1 min) addition reactions to the imine double bond of 2-(methylimino)acetate complexes [L(4)Co(O(2)CCH=NCH(3))](2+) [L(4) = (en)(2) (7), (tren) (11)] were achieved in aqueous solution with nitromethane, ethyl 3-oxobutanoate or diethyl malonate. The molecular structures of two product complexes, rac-(Δ*-R(C)*-S(N)*)-[Co(en)(2)(O(2)CCH[CH(2)NO(2)]NHCH(3))]ZnCl(4) and rac-(Δ*-R(C)*-S(N)*)-[Co(en)(2)(O(2)CCH[CH(2)COCH(3)]NHCH(3))]ZnCl(4), were established by X-ray diffraction.
authors.affiliation: Department of Chemistry, University of Copenhagen, DK-2100 Copenhagen Ø, Denmark.
authors.forename: Stephanie
authors.initials: S
authors.lastname: Oerum
authors.forename: Peter
authors.initials: P
authors.lastname: Krabbe
authors.forename: Magnus
authors.initials: M
authors.lastname: Schau-Magnussen
authors.forename: Søren
authors.initials: S
authors.lastname: Furbo
authors.forename: Jesper
authors.initials: J
authors.lastname: Bendix
authors.forename: Anders
authors.initials: A
authors.lastname: Hammershøi
mesh_terms: D000090:Acetoacetates / Q000737:chemistry; D003035:Cobalt / Q000737:chemistry*; D056831:Coordination Complexes / Q000138:chemical synthesis / Q000737:chemistry*; D018360:Crystallography, X-Ray; D008314:Malonates / Q000737:chemistry; D008352:Mannich Bases / Q000737:chemistry*; D008697:Methane / Q000031:analogs & derivatives / Q000737:chemistry; D008968:Molecular Conformation; D009595:Nitroparaffins / Q000737:chemistry; D013237:Stereoisomerism; D014867:Water / Q000737:chemistry*
chemical_list: D000090:Acetoacetates; D056831:Coordination Complexes; D008314:Malonates; D008352:Mannich Bases; D009595:Nitroparaffins; D014867:Water; D003035:Cobalt; C498810:diethyl malonate; C024840:ethyl acetoacetate; D008697:Methane; C008640:nitromethane