Journal article
Facile synthesis of α-aminoboronic acids from amines and potassium acyltrifluoroborates (KATs) via trifluoroborate-iminiums (TIMs).
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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.
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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.
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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.
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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.
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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.
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Language
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Open access status
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gold
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Identifiers
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Persistent URL
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https://sonar.ch/global/documents/176337
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