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Mechanistic Insight into the Facilitation of β‐Lactam Fragmentation through Metal Assistance
Author(s) -
Casarrubios Luis,
Esteruelas Miguel A.,
Larramona Carmen,
Lledós Agustí,
Muntaner Jaime G.,
Oñate Enrique,
Ortuño Manuel A.,
Sierra Miguel A.
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201503595
Subject(s) - facilitation , fragmentation (computing) , lactam , chemistry , neuroscience , psychology , biology , stereochemistry , ecology
The mechanism of OsH 6 (P i Pr 3 ) 2 ‐mediated fragmentation of a 4‐(2 pyridyl)‐2‐azetidinone has been investigated by DFT calculations. The addition of the C4H bond of the substrate to OsH 2 (P i Pr 3 ) 2 allows the active participation of an osmium lone pair in the B‐type β‐lactam fragmentation process. This new mechanism makes the N1C4/C2C3 fragmentation of the lactamic core thermally accessible through a stepwise process.