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    An Enantioselective Synthesis of S-(+)-Fluoxitine

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    Author
    Ross, Derek
    Issue
    urc_student; urc_student
    Date
    2006-01-01 0:00
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    URI
    https://scholar.oxy.edu/handle/20.500.12711/553
    Abstract
    An enatioselective sythesis of S-(+)-Fluoxitine is shown by utilizing the enzyme (R)-oxynitrilase to induce chirality, in high enantiomeric excess, in trans-cinnamaldehyde to form (R,E)-2-hydroxy-4-phenylbut-3-enenitrile. After converting the nitrile functionality to the ethyl ester thru a hydrolytic esterification, the hydoxy group is converted to the ethyl carbonate. Using tetrakis(triphenylphosphine)palladium(0) as a catalyst, the carbonate group is displaced and a 4-(trifluoromethyl)phenoxy group is instaled in a 1,3 substitutive chiral transfer to form (S,E)-ethyl 4-(4-(trifluoromethyl)phenoxy)-4-phenylbut-2-enoate. After subsequent reduction of the double bond and amidation of the ethyl ester, a Hoffman rearrangement is performed anhydrously in ethanol to form ethyl (S)-3-(4-(trifluoromethyl)phenoxy)-3-phenylpropylcarbamate. Subsequent reduction and treatment with HCl yields S-(+)-Fluoxitine as the hydrochloride salt.
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