Dynamic Kinetic Cross-Coupling Strategy for the Asymmetric Synthesis of Axially Chiral Heterobiaryls

作者:Ros Abel; Estepa Beatriz; Ramirez Lopez Pedro; Alvarez Eleuterio; Fernandez Rosario*; Lassaletta Jose M
来源:Journal of the American Chemical Society, 2013, 135(42): 15730-15733.
DOI:10.1021/ja4087819

摘要

A dynamic kinetic asymmetric transformation (DYKAT) technique has been designed for the synthesis of 2'-substituted 2-aryl pyridines/isoquinolines and related heterobiaryls. In this way, the Pd(0)-catalyzed coupling of racemic 2-triflates with aryl boroxines using a TADDOL-derived phosphoramidite as the ligand provides the corresponding coupling products with good to excellent enantioselectivities. Structural studies support that the formation of configurationally labile oxidative addition palladacycles is the key for the success of the methodology.

  • 出版日期2013-10-23