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Manganese(I)‐Catalyzed Access to Enantioenriched Chiral Aziridine Phosphines

Chao Ni, Tizian‐Frank Ramspoth, Marta Castiñeira Reis, Syuzanna R. Harutyunyan

2024Angewandte Chemie International Edition13 citationsDOIOpen Access PDF

Abstract

Herein, we present the first catalytic asymmetric nucleophilic addition of diarylphosphines to 2H-azirines, facilitated by a chiral Mn(I) complex. This method not only provides access to novel class of derivatives of the aziridine core - a structural motif recognized for its antitumor and antibacterial properties - but also introduces a phosphine moiety alongside the generation of an NH moiety within a strained three-membered ring. The discovery of this new Mn(I) complex that both enables the reaction and induces stereoselectivity is pivotal, as it underscores the significant potential of this earth-abundant metal in advancing asymmetric catalysis.

Topics & Concepts

AziridineMoietyEnantioselective synthesisNucleophilePhosphineChemistryCatalysisManganeseStereoselectivityCombinatorial chemistryStereochemistryDesymmetrizationRing (chemistry)Organic chemistrySynthesis and Catalytic ReactionsAsymmetric Hydrogenation and CatalysisCatalytic C–H Functionalization Methods
Manganese(I)‐Catalyzed Access to Enantioenriched Chiral Aziridine Phosphines | Litcius