Regiodivergent Ring-Opening Cross-Coupling of Vinyl Aziridines with Phosphorus Nucleophiles: Access to Phosphorus-Containing Amino Acid Derivatives

Published on 2018-11-08T21:44:01Z (GMT) by
Catalytic ring-opening phosphonation and phosphatation of vinyl aziridines have been developed in a regiodivergent fashion, giving linear and branched products. Generation of P-centered radicals enables S<sub>N</sub>2′-type ring-opening reactions of vinyl aziridines to afford δ-amino alkylphosphorus products at room temperature. On the other hand, in situ generated phosphate anions via the Ag-catalyzed aerobic oxidation of phosphonyl reactants underwent S<sub>N</sub>2 reaction to provide branched phosphorus-containing amine products. Furthermore, this divergent methodology serves as a powerful tool for the stereospecific synthesis of phosphorus-containing amino acid derivatives.

Cite this collection

Kang, Dahye; Kim, Taehwan; Lee, Hyunpyo; Hong, Sungwoo (2018): Regiodivergent Ring-Opening Cross-Coupling of Vinyl

Aziridines with Phosphorus Nucleophiles: Access to Phosphorus-Containing

Amino Acid Derivatives. ACS Publications. Collection.