PROCESS FOR PREPARING A CHIRAL TETRALONE

A process for preparing the chiral (4S)-(3,4-dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenone is disclosed wherein racemic 4-(3,4-dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenone is asymmetrically reduced by contacting the racemic tetralone with an asymmetric reagent to produce a mixture of cis and tr...

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Bibliographic Details
Main Author QUALLICH, GEORGE, J
Format Patent
LanguageEnglish
French
Published 08.06.1995
Edition6
Subjects
ACYCLIC OR CARBOCYCLIC COMPOUNDS
APPARATUS THEREFOR
CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOIDCHEMISTRY
CHEMISTRY
GENERAL METHODS OF ORGANIC CHEMISTRY
METALLURGY
ORGANIC CHEMISTRY
PERFORMING OPERATIONS
PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
THEIR RELEVANT APPARATUS
TRANSPORTING
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Summary:A process for preparing the chiral (4S)-(3,4-dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenone is disclosed wherein racemic 4-(3,4-dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenone is asymmetrically reduced by contacting the racemic tetralone with an asymmetric reagent to produce a mixture of cis and trans alcohols, separating the cis from the trans alcohols, and oxidizing the (4S) enantiomer of the resulting cis and trans alcohols. Also disclosed are novel intermediates used in the synthesis of the above chiral tetralone. Procédé de préparation de la (4S)-(3,4-dichlorophényl)-3,4-dihydro-1(2H)-naphtalénone chirale, selon lequel on réalise une réduction asymétrique de la 4-(3,4-dichlorophényl)-3,4-dihydro-1(2H)-naphtalénone racémique par mise en contact de la tétralone racémique avec un réactif asymétrique afin de produire un mélange d'alcools cis et trans, on sépare les alcools cis des alcools trans, et on provoque l'oxydation de l'énantiomère (4S) des alcools cis et trans ainsi obtenus. On a également prévu de nouveaux intermédiaires utilisés dans la synthèse de cette tétralone chirale.
Bibliography:Application Number: WO1994IB00263