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Synlett 1999; 1999(6): 765-767
DOI: 10.1055/s-1999-2712
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Enantioselective Synthesis of (R)- and (S)-Cizolirtine; Application of Oxazaborolidine-Catalyzed Asymmetric Borane Reduction to Azolyl Phenyl Ketones

Antoni Torrens* , José A. Castrillo, Alex Claparols, Jordi Redondo
  • *Department of Medicinal Chemistry, Laboratorios Dr. Esteve, Av. Mare de Déu de Montserrat 221, E-08041 Barcelona, Spain; Fax +34 93 4 50 16 11; E-mail: atorrens@esteve.es
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Publication Date:
31 December 1999 (online)

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An efficient enantioselective synthesis of (R)- and (S)-cizolirtine 1 is described. The key step of the procedure is the CBS-oxazaborolidine asymmetric reduction of phenyl pyrazolyl ketone 2. Related enantioselective reductions of several azolyl phenyl ketones are also reported.

asymmetric synthesis - cizolirtine - oxazaborolidine - azolyl phenyl ketones - enantioselective reduction