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

Author:
Nishikawa, Daiki, Hirano, Koji, Miura, Masahiro
Source:
Journal of the American Chemical Society 2015 v.137 no.50 pp. 15620-15623
ISSN:
1520-5126
Subject:
acids, catalytic activity, copper, enantiomers
Abstract:
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.
Agid:
5416860