Cargando…
Facile synthesis of α-aminoboronic acids from amines and potassium acyltrifluoroborates (KATs) via trifluoroborate-iminiums (TIMs)
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 impor...
Autores principales: | , , , |
---|---|
Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Royal Society of Chemistry
2018
|
Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6000978/ https://www.ncbi.nlm.nih.gov/pubmed/29997873 http://dx.doi.org/10.1039/c8sc01486h |
Sumario: | 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. |
---|