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Facile Synthesis of α-aminoboronic Acids From Amines and Potassium Acyltrifluoroborates (KATs)

Facile Synthesis of α-aminoboronic Acids From Amines and Potassium Acyltrifluoroborates (KATs)

Tomoya Shiro, Anne Schuhmacher, Moritz K Jackl, Jeffrey W Bode

Chem Sci. 2018 May 16;9(23):5191-5196.

PMID: 29997873

Abstract:

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.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP910251104	Potassium (tert-butoxymethyl)trifluoroborate		910251-10-4	Price

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