Synthesis of beta-lactams from a N-rhenaimine: effect of the transition metal on the energetic profile of the Staudinger reaction

E Hevia, J Perez, V Riera, D Miguel, P Campomanes, M I Menendez, T L Sordo, S Garcia-Granda

Research output: Contribution to journalArticle

31 Citations (Scopus)

Abstract

As depicted in the scheme, the alkylidenamido complex 1, a N-rhenaimine, reacts with ketenes to afford the β-lactams 2−4, which possess a {Re(CO)3(bpy)} fragment as substituent at nitrogen. Clean demetalations using HOTf or MeOTf yield the free β-lactams or N-methyl-β-lactams along with [Re(OTf)(CO)3(bpy)]. DFT calculations help to rationalize why the reaction is faster than those of non transition metal N-substituted imines.
LanguageEnglish
Pages3706-3707
Number of pages2
JournalJournal of the American Chemical Society
Volume125
Issue number13
DOIs
Publication statusPublished - 2 Apr 2003

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beta-Lactams
Transition metals
Metals
Carbon Monoxide
Imines
Discrete Fourier transforms
Nitrogen
Lactams

Keywords

  • imines
  • ketenes
  • beta-lactams

Cite this

Hevia, E ; Perez, J ; Riera, V ; Miguel, D ; Campomanes, P ; Menendez, M I ; Sordo, T L ; Garcia-Granda, S . / Synthesis of beta-lactams from a N-rhenaimine: effect of the transition metal on the energetic profile of the Staudinger reaction. In: Journal of the American Chemical Society. 2003 ; Vol. 125, No. 13. pp. 3706-3707.
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Synthesis of beta-lactams from a N-rhenaimine: effect of the transition metal on the energetic profile of the Staudinger reaction. / Hevia, E ; Perez, J ; Riera, V ; Miguel, D ; Campomanes, P ; Menendez, M I ; Sordo, T L ; Garcia-Granda, S .

In: Journal of the American Chemical Society, Vol. 125, No. 13, 02.04.2003, p. 3706-3707.

Research output: Contribution to journalArticle

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AU - Hevia, E

AU - Perez, J

AU - Riera, V

AU - Miguel, D

AU - Campomanes, P

AU - Menendez, M I

AU - Sordo, T L

AU - Garcia-Granda, S

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AB - As depicted in the scheme, the alkylidenamido complex 1, a N-rhenaimine, reacts with ketenes to afford the β-lactams 2−4, which possess a {Re(CO)3(bpy)} fragment as substituent at nitrogen. Clean demetalations using HOTf or MeOTf yield the free β-lactams or N-methyl-β-lactams along with [Re(OTf)(CO)3(bpy)]. DFT calculations help to rationalize why the reaction is faster than those of non transition metal N-substituted imines.

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