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Synthesis of Aminoboronic Acid Derivatives from Amines and Amphoteric Boryl Carbonyl Compounds
Authors:Diego B Diaz  Dr Conor C G Scully  Sean K Liew  Dr Shinya Adachi  Dr Piera Trinchera  Dr Jeffrey D St?Denis  Prof?Dr Andrei K Yudin
Institution:Davenport Research Laboratories, Department of Chemistry, University of Toronto, Toronto, ON, Canada
Abstract:Herein, we demonstrate the use of α‐boryl aldehydes and acyl boronates in the synthesis of aminoboronic acid derivatives. This work highlights the untapped potential of boron‐substituted iminium ions and offers insights into the behavior of N‐methyliminodiacetyl (MIDA) boronates during condensation and tautomerization processes. The preparative value of this contribution lies in the demonstration that various amines, including linear and cyclic peptides, can be readily conjugated with boron‐containing fragments. A mild deprotection of amino MIDA‐boronates enables access to α‐ and β‐aminoboronic acids in high chemical yields. This simple process should be applicable to the synthesis of a wide range of bioactive molecules as well as precursors for cross‐coupling reactions.
Keywords:boron  NMR spectroscopy  peptidomimetics  reaction kinetics  tautomerism
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