Chiral Phosphoric Acid–Palladium(II) Complex Catalyzed Asymmetric Desymmetrization of Biaryl Compounds by C(sp<sup>3</sup>)–H Activation
Tatsuhiro Uchikura, Sotaro Kato, Yudai Makino, M. FUJIKAWA, Masahiro Yamanaka, Takahiko Akiyama
Abstract
Desymmetrization is an essential method for the synthesis of chiral compounds, particularly chiral biaryls. We have developed an enantioselective synthesis of axially chiral biaryls by desymmetrization using C(sp 3 )–H activation catalyzed by chiral palladium phosphate. Mechanistic studies show that C–H activation is the rate- and enantiomer-determining step. To the best of our knowledge, this is the first report of asymmetric desymmetrization of axially chiral compounds by C(sp 3 )–H activation.
Topics & Concepts
DesymmetrizationChemistryEnantioselective synthesisPalladiumPhosphoric acidCatalysisEnantiomerStereochemistryAxial chiralityChiral auxiliaryCombinatorial chemistryOrganic chemistryAxial and Atropisomeric Chirality SynthesisCatalytic C–H Functionalization MethodsAsymmetric Synthesis and Catalysis