Cobalt‐Catalysed Asymmetric Addition and Alkylation of Secondary Phosphine Oxides for the Synthesis of <i>P</i>‐Stereogenic Compounds
Zeng‐Hua Wu, An‐Qi Cheng, Yuan Meng, Ya‐Xuan Zhao, Huai‐Lan Yang, Li‐Hua Wei, Huaiyu Wang, Tao Wang, Zun‐Ting Zhang, Wei‐Liang Duan
Abstract
The catalytic asymmetric synthesis of P-chiral phosphorus compounds is an important way to construct P-chiral ligands. Herein, we report a new strategy that adopts the pyridinyl moiety as the coordinating group in the cobalt-catalysed asymmetric nucleophilic addition/alkylation of secondary phosphine oxides. A series of tertiary phosphine oxides were generated with up to 99 % yield and 99.5 % ee, and with broad functional-group tolerance. Mechanistic studies reveal that (R)-secondary phosphine oxides preferentially interact with the cobalt catalysts to produce P-stereogenic compounds.
Topics & Concepts
StereocenterPhosphineCobaltAlkylationMoietyChemistryEnantioselective synthesisCatalysisNucleophileYield (engineering)Medicinal chemistryOrganic chemistryStereochemistryCombinatorial chemistryMaterials scienceMetallurgyAsymmetric Hydrogenation and CatalysisAsymmetric Synthesis and CatalysisSynthetic Organic Chemistry Methods