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 journalArticlepeer-review

19 Scopus citations

Abstract

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 (US)
Pages (from-to)16781-16785
Number of pages5
JournalChemistry - A European Journal
Volume21
Issue number47
DOIs
StatePublished - Nov 1 2015

Bibliographical note

Publisher Copyright:
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords

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

Fingerprint

Dive into the research topics of 'Mechanistic Insight into the Facilitation of β-Lactam Fragmentation through Metal Assistance'. Together they form a unique fingerprint.

Cite this