Enantioselective conjugate addition of a lithium ester enolate catalyzed by chiral lithium amides.
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]
Duguet
Nicolas
N
Laboratoire des Fonctions Azotées & Oxygénées Complexes de l'IRCOF, UMR CNRS 6014, Université et INSA de Rouen, 76821 Mont Saint-Aignan Cedex, France.
Harrison-Marchand
Anne
A
Maddaluno
Jacques
J
Tomioka
Kiyoshi
K
D000577:Amides / Q000737:chemistry; D002384:Catalysis; D008094:Lithium / Q000737:chemistry*; D009942:Organometallic Compounds / Q000138:chemical synthesis*; D011759:Pyrrolidines / Q000737:chemistry; D012997:Solvents; D013237:Stereoisomerism
D000577:Amides; D009942:Organometallic Compounds; D011759:Pyrrolidines; D012997:Solvents; D008094:Lithium