Facile synthesis of α-aminoboronic acids from amines and potassium acyltrifluoroborates (KATs) via trifluoroborate-iminiums (TIMs).
Journal article

Facile synthesis of α-aminoboronic acids from amines and potassium acyltrifluoroborates (KATs) via trifluoroborate-iminiums (TIMs).

  • Shiro T Laboratorium fur Organische Chemie , Department of Chemistry and Applied Biosciences , ETH Zurich , Zürich , Switzerland 8093 . Email: bode@org.chem.ethz.ch ; http://www.bode.ethz.ch.
  • Schuhmacher A Laboratorium fur Organische Chemie , Department of Chemistry and Applied Biosciences , ETH Zurich , Zürich , Switzerland 8093 . Email: bode@org.chem.ethz.ch ; http://www.bode.ethz.ch.
  • Jackl MK Laboratorium fur Organische Chemie , Department of Chemistry and Applied Biosciences , ETH Zurich , Zürich , Switzerland 8093 . Email: bode@org.chem.ethz.ch ; http://www.bode.ethz.ch.
  • Bode JW Laboratorium fur Organische Chemie , Department of Chemistry and Applied Biosciences , ETH Zurich , Zürich , Switzerland 8093 . Email: bode@org.chem.ethz.ch ; http://www.bode.ethz.ch.
Show more…
  • 2018-07-13
Published in:
  • Chemical science. - 2018
English We report the facile formation of trifluoroborate-iminiums (TIMs) from potassium acyltrifluoroborates (KATs) and the transformation of TIMs to α-aminotrifluoroborates by reduction or Grignard additions. Conditions for the hydrolysis of α-aminotrifluoroborates to α-aminoboronic acids, which are important biologically active compounds, were established. This new methodology allows access to sterically demanding α-aminoboronic acids that are not easily prepared with currently available methods. This work also introduces TIMs, that can be easily prepared and handled, as a new category of functional groups that serve as precursors to valuable organic compounds.
Language
  • English
Open access status
gold
Identifiers
Persistent URL
https://sonar.ch/global/documents/176337
Statistics

Document views: 8 File downloads: