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

Daiki Nishikawa; Koji Hirano; Masahiro Miura

doi:10.1021/jacs.5b09773

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

J Am Chem Soc. 2015 Dec 23;137(50):15620-3. doi: 10.1021/jacs.5b09773. Epub 2015 Dec 14.

Authors

Daiki Nishikawa¹, Koji Hirano¹, Masahiro Miura¹

Affiliation

¹ Department of Applied Chemistry, Graduate School of Engineering, Osaka University , Suita, Osaka 565-0871, Japan.

PMID: 26653275
DOI: 10.1021/jacs.5b09773

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.

Publication types

Research Support, Non-U.S. Gov't