Mechanistic Insight into the Facilitation of β-Lactam Fragmentation through Metal Assistance

Luis Casarrubios, Miguel A. Esteruelas, Carmen Larramona, Agustí Lledõs, Jaime G. Muntaner, Enrique Oñate, Manuel A. Ortuño, Miguel A. Sierra

Research output: Contribution to journalArticleResearchpeer-review

19 Citations (Scopus)

Abstract

© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. The mechanism of OsH6(PiPr3)2-mediated fragmentation of a 4-(2 pyridyl)-2-azetidinone has been investigated by DFT calculations. The addition of the C4-H bond of the substrate to OsH2(PiPr3)2 allows the active participation of an osmium lone pair in the B-type β-lactam fragmentation process. This new mechanism makes the N1-C4/C2-C3 fragmentation of the lactamic core thermally accessible through a stepwise process.
Original languageEnglish
Pages (from-to)16781-16785
JournalChemistry - A European Journal
Volume21
Issue number47
DOIs
Publication statusPublished - 1 Nov 2015

Keywords

  • azetidinone
  • density functional calculations
  • hexahydride
  • osmium
  • β-lactam fragmentation

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