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Promoted by Samarium Reaction of (3r,4r)-3-((1r)-1-{[Tert-Butyl(dimethyl)Silyl]oxy}Ethyl)-4-Acetoxy-Azetidin-2-one with Methyl 2-Bromopropianate. Unusual Decyclization of Azetidin-2-one Derivative in Approaches to Carbapenems Analogues

Author

Listed:
  • Zuleykha R Valiullina
  • Lidiya S Khasanova
  • Natalia K Selezneva
  • Yu N Belokon

    (Ufa Institute of Chemistry of the Russian Academy of Sciences, Russia)

  • Leonid V Spirikhin
  • Mansur S Miftakhov

    (AN Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences, Russia)

Abstract

The reaction of the title compound 1 with Sm-reagent prepared from powdered Sm, catalytic amounts of I2 and methyl 2-bromopropionate in THF, leads to the anomalous substituted product 3. The alkylation of the last compound with methyl bromoacetate gives methyl 2-[(2S,3S)-3-((1R)-1-{[tert-butyl(dimethyl) silyl]oxy}ethyl)-1-(2-methoxy-2-oxoethyl)-4-oxoazetidine-2-yl]-2-methyl-3-oxopentanoate 5 which under the action of NaHMDS in THF at -78° undergoes fragmentation with a disconnection of N1-C4-bond and the formation of acyclic amide 7. Possible stepwise formation routes of 3 and 7 are discussed.

Suggested Citation

  • Zuleykha R Valiullina & Lidiya S Khasanova & Natalia K Selezneva & Yu N Belokon & Leonid V Spirikhin & Mansur S Miftakhov, 2017. "Promoted by Samarium Reaction of (3r,4r)-3-((1r)-1-{[Tert-Butyl(dimethyl)Silyl]oxy}Ethyl)-4-Acetoxy-Azetidin-2-one with Methyl 2-Bromopropianate. Unusual Decyclization of Azetidin-2-one Derivative in ," Organic & Medicinal Chemistry International Journal, Juniper Publishers Inc., vol. 2(5), pages 108-112, June.
    • Handle: RePEc:adp:jomcij:v:2:y:2017:i:5:p:108-112
    DOI: 10.19080/OMCIJ.2017.02.555597
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