Asymmetric Synthesis of α‑Aminoboronic Acid Derivatives by Copper-Catalyzed Enantioselective Hydroamination

A copper-catalyzed
regio- and enantio­selective hydroamination
of alkenyl dan boronates (dan =1,8-diaminonaphthyl) with hydrosilanes
and hydroxylamines proceeds to deliver the chiral α-aminoboronic
acids in good yields with high enantiomeric ratios. The key to success
is the introduction of an umpolung, electrophilic amination strategy.
The copper catalysis can provide an unprecedented catalytic asymmetric
approach to alkyl-substituted chiral α-aminoboronic acid derivatives
of great potential in the fields of organic synthesis and medicinal
chemistry.