Abstract
Optically active α-aminoboronic acids, find widespread application in medicinal chemistry. . Herein, we present a straightforward synthetic strategy based on the enantioselective cross-coupling of readily available racemic α-chloro boronates with carbamates using an earth-abundant copper catalyst with a commercial chiral diamine and a diaryl phosphine as the ligands. These reaction conditions originated from a mechanistic study of a photoinduced system. Mechanistic investigations support that product formation occurs via kinetic resolution of the racemic α-chloro boronate. Moreover, the diaryl phosphine is alkylated by the electrophile under the reaction conditions forming α-phosphino boronates that act as the active ligand during catalysis.
Supplementary materials
Title
Supplementary Materials
Description
Contains all experimental details and characterizations of compounds including NMR and IR spectra and SFC traces to determine enantioselectivity.
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