A “green” ARGET-ATRC, for the CuCl[PMDETA] catalysed cyclo-isomerization of N-allyl-alpha-polychloroamides to γ-lactams is described. The process works efficiently (yields 78-96%), uses a bio-solvent, as ethanol, and exploits the reducing feature of ascorbic acid to limit, at a low level (2-4%), 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 temperatures (25-37 °C), relatively short reaction times (usually 5 h) and low solvent volumes (2 mmoles of substrate/mL of ethanol). The method, upon stoichiometric adjustment, was also used for the synthesis of alpha,beta-unsaturated-γ-lactams from N-(2-chloroallyl)-alpha-polychloroamides, via a tandem process involving an ATRC and a reductive [1,2]-elimination.

A green way to γ-lactams through a copper catalyzed ARGET-ATRC in ethanol and in the presence of ascorbic acid / R., Casolari; F., Felluga; V., Frenna; Ghelfi, Franco; U. M., Pagnoni; A. F., Parsons; D., Spinelli. - In: TETRAHEDRON. - ISSN 0040-4020. - STAMPA. - 67:2(2011), pp. 408-416. [10.1016/j.tet.2010.11.025]

A green way to γ-lactams through a copper catalyzed ARGET-ATRC in ethanol and in the presence of ascorbic acid

GHELFI, Franco;
2011

Abstract

A “green” ARGET-ATRC, for the CuCl[PMDETA] catalysed cyclo-isomerization of N-allyl-alpha-polychloroamides to γ-lactams is described. The process works efficiently (yields 78-96%), uses a bio-solvent, as ethanol, and exploits the reducing feature of ascorbic acid to limit, at a low level (2-4%), 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 temperatures (25-37 °C), relatively short reaction times (usually 5 h) and low solvent volumes (2 mmoles of substrate/mL of ethanol). The method, upon stoichiometric adjustment, was also used for the synthesis of alpha,beta-unsaturated-γ-lactams from N-(2-chloroallyl)-alpha-polychloroamides, via a tandem process involving an ATRC and a reductive [1,2]-elimination.
2011
67
2
408
416
A green way to γ-lactams through a copper catalyzed ARGET-ATRC in ethanol and in the presence of ascorbic acid / R., Casolari; F., Felluga; V., Frenna; Ghelfi, Franco; U. M., Pagnoni; A. F., Parsons; D., Spinelli. - In: TETRAHEDRON. - ISSN 0040-4020. - STAMPA. - 67:2(2011), pp. 408-416. [10.1016/j.tet.2010.11.025]
R., Casolari; F., Felluga; V., Frenna; Ghelfi, Franco; U. M., Pagnoni; A. F., Parsons; D., Spinelli
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11380/648673
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