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Ruthenium‐Catalyzed Enantioselective Propargylic Phosphinylation of Propargylic Alcohols with Phosphine Oxides

Shiyao Liu, Yoshiaki Tanabe, Shogo Kuriyama, Ken Sakata, Yoshiaki Nishibayashi

2021Angewandte Chemie International Edition61 citationsDOI

Abstract

The development of transition metal-catalyzed enantioselective propargylic substitution reactions has gained much progress in recent years, however, no successful example with phosphorus-centered nucleophiles has yet been reported until now. Herein, we report the first successful example of ruthenium-catalyzed enantioselective propargylic substitution reactions of propargylic alcohols with diarylphosphine oxides as phosphorus-centered nucleophiles. This synthetic approach provides a new method to prepare chiral phosphorus-containing organic compounds.

Topics & Concepts

Enantioselective synthesisPhosphineRutheniumNucleophileCatalysisChemistryOrganic chemistryPhosphorusSubstitution reactionCombinatorial chemistryTransition metalAsymmetric Hydrogenation and CatalysisCatalytic C–H Functionalization MethodsOrganophosphorus compounds synthesis
Ruthenium‐Catalyzed Enantioselective Propargylic Phosphinylation of Propargylic Alcohols with Phosphine Oxides | Litcius