title: Enantio- and diastereoselective synthesis of substituted tetrahydro-1H-isochromanes through a dynamic kinetic resolution proceeding under dienamine catalysis.
abstract: Racemic 5-acyloxydihydropyranones react with enolizable α,β-unsaturated aldehydes in the presence of a chiral secondary amine catalyst furnishing a wide range of differently substituted tetrahydro-1H-isochromanes with excellent results. The reaction relies on the activation of the enal by the catalyst through the formation of a dienamine intermediate, which undergoes a Diels-Alder/elimination cascade reaction. Moreover, the overall transformation also results in a highly efficient dynamic kinetic resolution process, furnishing the final adducts in high yields and excellent diastereo- and enantioselectivities.
authors: Departamento de Química Orgánica II, Facultad de Ciencia y Tecnología, Universidad del País Vasco/Euskal Herriko Unibertsitatea UPV/EHU , P.O. Box 644, E-48080 Bilbao, Spain.
authors: Ane
authors: A
authors: Orue
authors: Efraím
authors: E
authors: Reyes
authors: Jose L
authors: JL
authors: Vicario
authors: Luisa
authors: L
authors: Carrillo
authors: Uxue
authors: U
authors: Uria