Enantioselective Synthesis of (S)-3-Hydroxy-3-phenyl-3,4-dihydroquinolin-2(1H)-one Ring System

Abstract

A series of new enantiomerically pure (S)-3-hydroxy-3phenyl-3,4-dihydroquinolin-2(1H)-ones was prepared in good yields according to a two-step synthesis using a benzylation of the sodium enolate of the (2S,5S)-cis-2-tert-butyl-5-phenyl-1,3-dioxolan-4-one with substituted o-nitrobenzyl bromides followed by reduction of the nitro group to amine with concomitant intramolecular aminolysis of the dioxolanone ring.