A green way to g-lactams through a copper catalyzed ARGET-ATRC in ethanoland in the presence of ascorbic acid

Vincenzo Frenna, Roberto Casolari, Fulvia Felluga, Ugo M. Pagnoni, Franco Ghelfi, Domenico Spinelli, Andrew F. Parsons

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Abstract

A ‘green’ ARGET-ATRC, for the CuCl[PMDETA] catalysed cyclo-isomerization of N-allyl-a-polychloroamides to g-lactams is described. The process works efficiently (yields 78e96%), uses a bio-solvent, as ethanol, and exploits the reducing feature of ascorbic acid to limit, at a low level (2e4%), the amount of catalyst. To preserve the efficacy of the catalytic cycle, addition of Na2CO3 is essential, which quenches the HCl released during the CuCl[PMDETA] regeneration step. Profitable features of the process are: mild reaction tem-peratures (25e37 C), relatively short reaction times (usually 5 h) and low solvent volumes (2 mmol of substrate/mL of ethanol). The method, upon stoichiometric adjustment, was also used for the synthesis of a,b-unsaturated-g-lactams from N-(2-chloroallyl)-a-polychloroamides, via a tandem process involving an ATRC and a reductive [1,2]-elimination.
Lingua originaleEnglish
pagine (da-a)408-416
Numero di pagine9
RivistaTetrahedron
Volume67
Stato di pubblicazionePublished - 2011

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All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cita questo

Frenna, V., Casolari, R., Felluga, F., Pagnoni, U. M., Ghelfi, F., Spinelli, D., & Parsons, A. F. (2011). A green way to g-lactams through a copper catalyzed ARGET-ATRC in ethanoland in the presence of ascorbic acid. Tetrahedron, 67, 408-416.