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Regiodivergent Ring-Opening Cross-Coupling of Vinyl Aziridines with Phosphorus Nucleophiles: Access to Phosphorus-Containing Amino Acid Derivatives
journal contribution
posted on 2018-11-02, 14:50 authored by Dahye Kang, Taehwan Kim, Hyunpyo Lee, Sungwoo HongCatalytic
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
SN2′-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 SN2
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.