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Asymmetric Synthesis of SCF 3 -Substituted Alkylboronates by Copper-Catalyzed Hydroboration of 1-Trifluoromethylthioalkenes.

Yuki KojimaYuji NishiiKoji Hirano
Published in: Angewandte Chemie (International ed. in English) (2024)
A synthetic method for preparation of optically active trifluoromethylthio (SCF 3 ) compounds by a copper-catalyzed regio- and enantioselective hydroboration of 1-trifluoromethylthioalkenes with H-Bpin has been developed. The enantioselective hydrocupration of an in situ generated CuH species and subsequent boration reaction generate a chiral SCF 3 -containing alkylboronate, of which Bpin moiety can be further transformed to deliver various optically active SCF 3 molecules. Computational studies suggest that the SCF 3 group successfully controls the regioselectivity in the reaction.
Keyphrases
  • mass spectrometry
  • ionic liquid
  • tandem mass spectrometry