Mechanistic Insight into the Facilitation of β‐Lactam Fragmentation through Metal Assistance | Zendy

Casarrubios Luis | Zendy; Esteruelas Miguel A. | Zendy; Larramona Carmen | Zendy; Lledós Agustí | Zendy; Muntaner Jaime G. | Zendy; Oñate Enrique | Zendy; Ortuño Manuel A. | Zendy; Sierra Miguel A. | Zendy

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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.

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