title: Enantioselective conjugate addition of a lithium ester enolate catalyzed by chiral lithium amides.
abstract: Mixed aggregates of chiral lithium amide and lithium ester enolate have been employed in the enantioselective conjugate addition on alpha,beta-unsaturated esters. Michael adducts were obtained in ee's up to 76% combining a lithium enolate and a chiral 3-aminopyrrolidine lithium amide. The sense of the induction was found to be determined by both the relative configuration of the stereogenic centers borne by the amide and the solvent in which the reaction was conducted. [reaction: see text]
authors.affiliation: Laboratoire des Fonctions Azotées & Oxygénées Complexes de l'IRCOF, UMR CNRS 6014, Université et INSA de Rouen, 76821 Mont Saint-Aignan Cedex, France.
authors.forename: Nicolas
authors.initials: N
authors.lastname: Duguet
authors.forename: Anne
authors.initials: A
authors.lastname: Harrison-Marchand
authors.forename: Jacques
authors.initials: J
authors.lastname: Maddaluno
authors.forename: Kiyoshi
authors.initials: K
authors.lastname: Tomioka
mesh_terms: D000577:Amides / Q000737:chemistry; D002384:Catalysis; D008094:Lithium / Q000737:chemistry*; D009942:Organometallic Compounds / Q000138:chemical synthesis*; D011759:Pyrrolidines / Q000737:chemistry; D012997:Solvents; D013237:Stereoisomerism
chemical_list: D000577:Amides; D009942:Organometallic Compounds; D011759:Pyrrolidines; D012997:Solvents; D008094:Lithium