Title:Removal of the Chiral Inductor from Phenylglycinol-derived Tricyclic Lactams. Unexpected Generation of Chiral trans-Hydrochromene Lactones
Volume: 15
Issue: 5
Author(s): Rosa Griera, Alexandre Pinto, Robert Fabregat, Eric Cots, Joan Bosch and Mercedes Amat*
Affiliation:
- Laboratory of Organic Chemistry, Faculty of Pharmacy and Food Sciences, Institute of Biomedicine (IBUB), University of Barcelona, 08028-Barcelona,Spain
Keywords:
Decahydroquinoline, debenzylation, lactams, lactones, perhydrochromene, sodium-ammonia.
Abstract: In the search for synthetic routes for the preparation of cis- and trans- decahydroquinolin-2-
ones, a procedure for the generation of enantiopure trans-hydrochromene lactones, by treatment of (R)-
phenylglycinol-derived oxazoloquinolone lactams with Na/liq. NH3 followed by acidification, has been
developed.