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Synthesis 2007(1): 108-112  
DOI: 10.1055/s-2006-958928
PAPER
© Georg Thieme Verlag Stuttgart · New York

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

Gonzalo Blay, Luz Cardona, Lucas Torres, José R. Pedro*
Departament de Química Orgànica, Facultat de Química, Universitat de València, 46100 Burjassot (València), Spain
Fax: +34963544329; e-Mail: jose.r.pedro@uv.es;
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Publication History

Received 1 August 2006
Publication Date:
12 December 2006 (online)

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Abstract

A series of new enantiomerically pure (S)-3-hydroxy-3-phenyl-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.

Key words

acetals - quinolines - alkylations - ring closure - diaste­reo­selectivity