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

• DOI: 10.1021/acs.orglett.8b03309
• Publication Date: 2018-11-02T14:53:11Z
• Authors: Dahye Kang; Taehwan Kim; Hyunpyo Lee; Sungwoo Hong
• Keywords: SN2 reaction; Stereospecificity

Catalytic ring-opening phosphonation and phosphatation of vinyl aziridines have been developed in a regiodivergent fashion, giving linear branched products. Generation P-centered radicals enables SN2′-type reactions to afford δ-amino alkylphosphorus products at room temperature. On the other hand, situ generated phosphate anions via Ag-catalyzed aerobic oxidation phosphonyl reactants underwent SN2 reaction provide phosphorus-containing amine Furthermore, this divergent methodology serves as powerful tool for stereospecific synthesis amino acid derivatives.