biostudies-literatureUnknown14(6)Zhu JThe enantioselective addition of arylboronic acids to <i>N</i>-heteroaryl ketones provides a convenient access to chiral α-heteroaryl tertiary alcohols, yet addition reactions of this type have been challenging due to catalyst deactivation. In this report, an efficient rhodium-catalyzed addition of arylboronic acids to <i>N</i>-heteroaryl ketones is established, affording a variety of valuable α-heteroaryl alcohols with excellent functional group compatibility. The employment of the WingPhos ligand containing two anthryl groups is crucial for this transformation. In particular, a range of chiral benzoxazolyl-substituted tertiary alcohols were formed with excellent <i>ee</i> values and yields by employing a Rh loading as low as 0.3 mol%, which can serve as a practical protocol to furnish a series of chiral α-hydroxy acids after hydrolysis.Chemical science1606-1612https://www.ebi.ac.uk/biostudies/studies/S-EPMC9906643biostudies-literatureEnantioselective rhodium-catalyzed addition of arylboronic acids to <i>N</i>-heteroaryl ketones: synthesis of α-hydroxy acids.PMC9906643Li ZLi JZhu JChen ZXu RTan ZTian DTang WfalseEnantioselective rhodium-catalyzed addition of arylboronic acids to <i>N</i>-heteroaryl ketones: synthesis of α-hydroxy acids.The enantioselective addition of arylboronic acids to <i>N</i>-heteroaryl ketones provides a convenient access to chiral α-heteroaryl tertiary alcohols, yet addition reactions of this type have been challenging due to catalyst deactivation. In this report, an efficient rhodium-catalyzed addition of arylboronic acids to <i>N</i>-heteroaryl ketones is established, affording a variety of valuable α-heteroaryl alcohols with excellent functional group compatibility. The employment of the WingPhos ligand containing two anthryl groups is crucial for this transformation. In particular, a range of chiral benzoxazolyl-substituted tertiary alcohols were formed with excellent <i>ee</i> values and yields by employing a Rh loading as low as 0.3 mol%, which can serve as a practical protocol to furnish a series of chiral α-hydroxy acids after hydrolysis.2023-01-01T00:00:00Z2023 Feb2025-04-04T11:16:54.88Z2025-04-04T11:16:54.88ZS-EPMC99066433679419810.1039/d2sc05907j