Now showing 1 - 3 of 3
  • Publication
    A concise flow synthesis of indole-3-carboxylic ester and its derivatisation to an auxin mimic
    (Beilstein-Institut, 2017-11-29) ; ;
    An assembled suite of flow-based transformations have been used to rapidly scale-up the production of a novel auxin mimic-based herbicide which was required for preliminary field trials. The overall synthetic approach and optimisation studies are described along with a full description of the final reactor configurations employed for the synthesis as well as the downstream processing of the reaction streams.
      54Scopus© Citations 14
  • Publication
    Diastereoselective Synthesis and Diversification of Highly Functionalized Cyclopentanones
    (Georg Thieme, 2018-02-15) ;
    An efficient entry into highly substituted cyclopentanones is presented based on functionalizing cyclopentenones by means of an aza-Michael reaction with different aniline nucleophiles. The excellent diastereoselectivity of this process is ascribed to H-bonding between a tertiary alcohol and the incoming nucleophiles. Additionally, the functionalization of the parent cyclopentenones via the Baylis-Hillman reaction is demonstrated. Together, these transformations showcase the elaboration of a simple precursor by installation of versatile functionalities at either the α- or β-position of the embedded enone and thus represent valuable methods for the construction of diversely functionalized cyclopentanones.
      66Scopus© Citations 1
  • Publication
    Unprecedented Alkene Transposition in Phthalate-Amino Acid Adducts
    A detailed account on the outcome of the thermal reaction between benzylidene phthalides and various amino acid derivatives is reported. It was discovered that the tricyclic pyrroles as previously described are not the products formed in these reactions. Instead under high-temperature conditions decarboxylated phthalamide adducts are formed within 5-10 minutes. Additionally, an unprecedented alkene transposition mechanism has been identified leading to the final products of these reactions.
      56Scopus© Citations 1