Browsing by Author "Durucasu İ."

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    Asymmetric synthesis of (S)-dihydrokavain from l-malic acid
    (Taylor and Francis Inc., 2018) Eskici M.; Karanfil A.; Özer M.S.; Kabak Y.; Durucasu İ.
    A practical and efficient asymmetric synthesis of (S)-dihydrokavain from known ethyl (S)-2-hydroxy-4-phenylbutanoate which is, in turn, readily available from l-malic acid as a cheap chiral pool material is described using regioselective ring-opening of the 1,2-cyclic sulfate with lithium-3,3,3-triethoxypropiolate and subsequent HgO/H2SO4-mediated lactonization as the key steps. Its opposite enantiomer (R)-dihydrokavain was also synthesized from d-malic acid using the same sequences of reactions for the purpose of optical purity determination. © 2018, © 2018 Taylor & Francis.