alpha-Aminoboronates: recent advances in their preparation and synthetic applications

alpha-Aminoboronic acids and their derivatives are useful as bioactive agents. Thus far, three compounds containing an alpha-aminoboronate motif have been approved by the Food and Drug Administration (FDA) as protease inhibitors, and more are currently undergoing clinical trials. In addition, alpha-aminoboronic acids and their derivatives have found applications in organic synthesis, e.g. as alpha-aminomethylation reagents for the synthesis of chiral nitrogen-containing molecules, as nucleophiles for preparing valuable vicinal amino alcohols, and as bis-nucleophiles in the construction of valuable small molecule scaffolds. This review summarizes new methodology for the preparation of alpha-aminoboronates, including highlights of asymmetric synthetic methods and mechanistic explanations of reactivity. Applications of alpha-aminoboronates as versatile synthetic building blocks are also discussed.

Automated summary

Alpha-aminoboronic acids and their derivatives are widely used as bioactive agents, with several compounds approved by the FDA as protease inhibitors. In organic synthesis, they are important reagents for the synthesis of chiral molecules and valuable organic compounds.