1384931-07-0Relevant academic research and scientific papers
Enantio- and diastereoselective synthesis of substituted tetrahydro-1H-isochromanes through a dynamic kinetic resolution proceeding under dienamine catalysis
Orue, Ane,Reyes, Efraim,Vicario, Jose L.,Carrillo, Luisa,Uria, Uxue
supporting information; experimental part, p. 3740 - 3743 (2012/08/28)
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.
