Dynamic Kinetic Cross-Coupling Strategy for the Asymmetric Synthesis of Axially Chiral Heterobiaryls
Journal of the American Chemical Society2013Vol. 135(42), pp. 15730–15733
Citations Over TimeTop 10% of 2013 papers
Abel Ros, Beatriz Estepa, Pedro Ramírez‐López, Eleuterio Álvarez, Rosario Fernández, José M. Lassaletta
Abstract
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.
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