Enantioselective Synthesis of α-Aminoboronic Acid Derivatives via Copper-Catalyzed N-Alkylation

By Giuseppe Zuccarello, Suzanne M. Batiste, Hyungdo Cho, and Gregory C. Fu

February 24, 2023

  • Year

  • Technique

  • Industry

Title

Enantioselective Synthesis of α-Aminoboronic Acid Derivatives via Copper-Catalyzed N-Alkylation

Author

Giuseppe Zuccarello, Suzanne M. Batiste, Hyungdo Cho, and Gregory C. Fu

Year

2023

Journal

ACS publications

Abstract

Due to burgeoning interest in the pharmaceutical industry in exploiting optically active α-aminoboronic derivatives as bioisosteres of α-amino acid derivatives, the discovery of methods for their catalytic asymmetric synthesis is an important challenge. Herein, we establish that a chiral copper catalyst (generated in situ from commercially available components) can achieve the enantioselective synthesis of α-aminoboronic derivatives via the coupling of two readily available partners, a carbamate and a racemic α-chloroboronate ester. Furthermore, we describe mechanistic studies that played a key role in the development of this new method and that provide insight into the optimized process.

Full Article

https://pubs.acs.org/doi/10.1021/jacs.3c00038

Instrument

P-2000

Keywords

pharmaceuticals, enantioselective,