Removal of the Chiral Inductor from Phenylglycinol-derived Tricyclic Lactams. Unexpected Generation of Chiral trans-Hydrochromene Lactones

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.

Cite this article as:

Griera Rosa , Pinto Alexandre , Fabregat Robert , Cots Eric , Bosch Joan and Amat Mercedes *, Removal of the Chiral Inductor from Phenylglycinol-derived Tricyclic Lactams. Unexpected Generation of Chiral trans-Hydrochromene Lactones, Letters in Organic Chemistry 2018; 15 (5) . https://dx.doi.org/10.2174/1570178615666171213143657