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

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Title
Regiodivergent Ring-Opening Cross-Coupling of Vinyl Aziridines with Phosphorus Nucleophiles: Access to Phosphorus-Containing Amino Acid Derivatives
Author(s)
Dahye Kang; Taehwan Kim; Hyunpyo Lee; Sungwoo Hong
Publication Date
2018-12
Journal
ORGANIC LETTERS, v.20, no.23, pp.7571 - 7575
Publisher
AMER CHEMICAL SOC
Abstract
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 © 2018 American Chemical Society
URI
https://pr.ibs.re.kr/handle/8788114/5913
DOI
10.1021/acs.orglett.8b03309
ISSN
1523-7060
Appears in Collections:
Center for Catalytic Hydrocarbon Functionalizations(분자활성 촉매반응 연구단) > 1. Journal Papers (저널논문)
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