• Preparation of Rearranged Allylic Isocyanates from the Reaction of Allylic Alcohols with 1-Cyano-4-dimethylaminopyridinium Bromide

      Baidilov, Daler; Makarova, Mariia; Rycek, Lukas; Hudlicky, Tomas (Thieme, 2018-10-11)
      A shorter and less costly alternative to Ichikawa’s [1,3]-transposition protocol for cyanates to isocyanates is described.
    • Repetition of chemistry from a recently retracted paper. A cautionary note.

      Bedard, Korey; Ryan, Wilson; Baidilov, Daler; Tius, Marcus; Hudlicky, Tomas (Elsevier, 2018-06-20)
      The base-catalyzed condensation reaction between (E)-4-phenylbut-2-enal and phenylpropargyl aldehyde recently reported in the literature to provide formylcyclobutadiene was repeated under the published conditions. The product obtained was identified as (E)-5-phenyl-2-((E)-styryl)pent-2-en-4-ynal rather than the reported 2-phenyl-3-styrylcyclobutadiene-1-carboxaldehyde. The structure assignment is supported by NMR and IR data and a x-ray structure of the crystalline alcohol obtained by Luche reduction.
    • Sequential enzymatic and electrochemical functionalization of bromocyclohexadienediols: Application to the synthesis of (-)-conduritol C

      Hudlicky, Tomas; Goulart Stollmaier, Juana (Elsevier, 2020-02-14)
      cis-Diene diol obtained from the microbial oxidation of bromobenzene was used as a substrate for the chemoenzymatic acetylation and epoxidation with lipases. The model studies showed that the regiochemistry of the acetylation is solvent-dependent. The chemoenzymatic epoxidation followed the expected regiochemistry when compared to the chemical epoxidation with m-CPBA, but with the unexpected formation of bromoconduritol-C, an important intermediate whose electrochemical reduction led to the synthesis of (-)-conduritol-C. Experimental and spectral data are provided for all new compounds.