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

doi:10.1055/s-2006-958928

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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;

Abstract

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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

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References

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