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

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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(N)2'-type ring-opening reactions of vinyl aziridines to afford delta-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(N)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.
Publisher
AMER CHEMICAL SOC
Issue Date
2018-12
Language
English
Article Type
Article
Citation

ORGANIC LETTERS, v.20, no.23, pp.7571 - 7575

ISSN
1523-7060
DOI
10.1021/acs.orglett.8b03309
URI
http://hdl.handle.net/10203/249008
Appears in Collection
CH-Journal Papers(저널논문)
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