Synthesis of Aminoboronic Acid Derivatives from Amines and Amphoteric Boryl Carbonyl Compounds
| Autor: | Diego B. Diaz, Piera Trinchera, Shinya Adachi, Sean K. Liew, Andrei K. Yudin, Conor C. G. Scully, Jeffrey D. St. Denis |
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| Rok vydání: | 2016 |
| Předmět: |
inorganic chemicals
chemistry.chemical_classification Aldehydes Molecular Structure 010405 organic chemistry Chemistry Peptidomimetic Bioactive molecules Iminium Stereoisomerism General Medicine General Chemistry Nuclear magnetic resonance spectroscopy Conjugated system 010402 general chemistry 01 natural sciences Tautomer Boronic Acids Catalysis Cyclic peptide 0104 chemical sciences Chemical kinetics Organic chemistry Amines |
| Zdroj: | Angewandte Chemie (International ed. in English). 55(41) |
| ISSN: | 1521-3773 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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