A Straightforward Synthesis of Functionalized <i>cis</i>-Perhydroisoquinolin-1-ones
Federica Arioli,
Maria Pérez,
Celeste Are,
Elies Molins,
Joan Bosch,
Mercedes Amat
Affiliations
Federica Arioli
Laboratory of Organic Chemistry, Faculty of Pharmacy and Food Sciences, and Institute of Biomedicine (IBUB), University of Barcelona, 08028 Barcelona, Spain
Maria Pérez
Department of Nutrition, Food Sciences and Gastronomy, Faculty of Pharmacy and Food Sciences, and Institute of Nutrition and Food Safety (INSA-UB), University of Barcelona, 08921 Santa Coloma de Gramanet, Spain
Celeste Are
Laboratory of Organic Chemistry, Faculty of Pharmacy and Food Sciences, and Institute of Biomedicine (IBUB), University of Barcelona, 08028 Barcelona, Spain
Elies Molins
Institut de Ciència de Materials de Barcelona (ICMAB-CSIC), Campus UAB, 08193 Cerdanyola, Spain
Joan Bosch
Laboratory of Organic Chemistry, Faculty of Pharmacy and Food Sciences, and Institute of Biomedicine (IBUB), University of Barcelona, 08028 Barcelona, Spain
Mercedes Amat
Laboratory of Organic Chemistry, Faculty of Pharmacy and Food Sciences, and Institute of Biomedicine (IBUB), University of Barcelona, 08028 Barcelona, Spain
Base-catalyzed annulation reactions of 5,6-dihydro-2(1H)-pyridones with Nazarov-type reagents are reported. The effect of the solvent polarity and the concentration of the reagents is studied. The process involves two successive Michael additions and stereoselectively provides functionalized cis-perhydroisoquinolin-1-ones.
