Asymmetric Conjugate Addition of Phosphonates to Enones Using Cinchona–Diaminomethylenemalononitrile Organocatalysts
Ryoga Arai, Shin‐ichi Hirashima, Tatsuki Nakano, Masahiro Kawada, Hiroshi Akutsu, Kosuke Nakashima, Tsuyoshi Miura
Abstract
-crotonophenone and chalcone derivatives using a diaminomethylenemalononitrile organocatalyst resulted in the generation of the corresponding chiral γ-ketophosphonates in high yields with excellent enantioselectivities (up to 95% ee). This report is the first successful example of asymmetric 1,4-additions of phosphonate to α,β-unsaturated ketones using an organocatalyst.
Topics & Concepts
ChemistryConjugatePhosphonateChalconeCinchonaOrganocatalysisEnantioselective synthesisOrganic chemistryAddition reactionCatalysisCombinatorial chemistryMathematical analysisMathematicsOrganophosphorus compounds synthesisAsymmetric Hydrogenation and CatalysisAsymmetric Synthesis and Catalysis