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

32 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.
Original languageEnglish
Pages (from-to)3706-3707
Number of pages2
JournalJournal of the American Chemical Society
Volume125
Issue number13
DOIs
Publication statusPublished - 2 Apr 2003

Keywords

  • imines
  • ketenes
  • beta-lactams

Fingerprint Dive into the research topics of 'Synthesis of beta-lactams from a N-rhenaimine: effect of the transition metal on the energetic profile of the Staudinger reaction'. Together they form a unique fingerprint.

Cite this