title: One-pot sequential organocatalytic Michael-Tishchenko-lactonization reactions. Synthesis of enantioenriched 4,5,6-trisubstituted δ-lactones.
abstract: Enantioenriched trisubstituted lactones were obtained in good yields and moderate to very good enantioselectivities in one-pot process, which implies a sequential organocatalyzed Michael addition of ketones to enals, followed by catalytic intramolecular diastereoselective Tishchenko reaction and lactonization. The final lactones were obtained as single diastereoisomers, demonstrating that the mixture of the anti and syn diastereomers epimerized to the syn hydroxy ester during the oxido-reduction step.
authors.affiliation: Instituto CINQUIMA and Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Valladolid , Paseo de Belén 7, 47011 Valladolid, Spain.
authors.forename: James O
authors.initials: JO
authors.lastname: Guevara-Pulido
authors.forename: José M
authors.initials: JM
authors.lastname: Andrés
authors.forename: Rafael
authors.initials: R
authors.lastname: Pedrosa
mesh_terms: D002384:Catalysis; D004952:Esters; D007659:Ketones / Q000737:chemistry*; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D010084:Oxidation-Reduction; D013237:Stereoisomerism
chemical_list: D004952:Esters; D007659:Ketones; D007783:Lactones