An Update on the Synthesis of &amp;#946;-Lactams

Aranda, M. Teresa; Perez‐Faginas, Paula; González‐Muñiz, Rosario

doi:10.2174/157017909788921899

Cited by 64 publications

(9 citation statements)

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“…The neverending fight of mankind with bacteria has taken advantage of the evolutionary arsenal provided by fungi (one of the natural enemies of the bacteria) in the form, among others, of β-lactam antibiotics . However, the evolutionary pressure derived from the indiscriminate use of such as antibacterial agents has resulted in the apparition of bacteria strains capable of resisting the action, not only of the commonly used antibiotics but also of many of their synthetic analogues .…”

Section: Introductionmentioning

confidence: 99%

Chelated Assisted Metal-Mediated N–H Bond Activation of β-Lactams: Preparation of Irida-, Rhoda-, Osma-, and Ruthenatrinems

et al. 2014

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2-Azetidinones substituted with pyridine (2a), quinoline (2b), isoquinoline (2c), imidazole (2d), and benzimidazole (2e) at the 4-position of the four-membered ring have been prepared in order to synthesize tribactams containing a transition metal and its associated ligands, L n M, at the 2-position of the tricyclic skeleton. The developed procedure is compatible with a wide range of transition-metal starting complexes. Thus, the iridium and rhodium dimers [M(η 5 -C 5 Me 5 )Cl 2 ] 2 react with 2a−e, in the presence of sodium acetate, to afford irida-and rhodatrinems (1a−j) containing the half-sandwich d 6 metal fragments M(η 5 -C 5 Me 5 )Cl (M = Ir, Rh). The reactions of [M(μ-OMe)(η 4 -COD)] 2 (M = Ir, Rh) with 2a lead to irida-and rhodatrinems (1k,l) with the d 8 moieties M(η 4 -COD). The coordination sphere and oxidation state of the metal center in these compounds can be modified, without affecting the 2-azetidinone backbone, by means of substitution and oxidative addition reactions. As a proof of concept, metallatrinems with the M(CO) 2 (M = Ir (1m), Rh (1n)) and Ir(Me)I(CO) 2 (1o) units are also reported. Osmatrinems 1p,q containing the d 4 metal fragment OsH 3 (P i Pr 3 ) 2 have been obtained starting from the d 2 hexahydride OsH 6 (P i Pr 3 ) 2 , by reaction with 2a,b, whereas the treatment of the tetrahydroborate complexes MH(η 2 -H 2 BH 2 )(CO)(P i Pr 3 ) 2 (M = Os, Ru) with 2a yields osma-and ruthenatrinems (1r,s) containing six-coordinate bis(phosphine) d 6 metal fragments. The IR stretching frequency of the lactamic carbonyl, the bent angle between the fiveand four-membered rings of the tricycle, and the N−CO bond length in the lactamic ring are clearly infuenced by the L n M fragment.

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Section: Introductionmentioning

confidence: 99%

Chelated Assisted Metal-Mediated N–H Bond Activation of β-Lactams: Preparation of Irida-, Rhoda-, Osma-, and Ruthenatrinems

et al. 2014

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“…β-Lactams (azetidin-2-ones) are widely known both as pharmaceuticals (e.g., antibiotics and cholesterol-lowering drugs) and as versatile intermediates in the preparation of other classes of organic compounds . Enantioselective approaches to their synthesis, despite the many advances achieved in this field, remain limited in their scope. Therefore, enzymatic kinetic resolution (KR) of their racemates, mostly via β-lactam ring opening or O-acylation of N -hydroxymethyl derivatives, continues to be widely used (Figure ). , Enantioselective N-acylation, which would provide an alternative direct method for the KR of N-unsubstituted β-lactams, has not been previously reported.…”

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confidence: 99%

Kinetic Resolution of β-Lactams via Enantioselective N-Acylation

2011

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“…[326][327][328][329] Intramolecular N-acylation strategies are extremely useful for the synthesis of β-, γ-, and δ-lactams, with intramolecular variants of many intermolecular amide bond-forming processes having been demonstrated. The intramolecular cyclization of β-amino acids into β-lactams is an attractive strategy for the synthesis of highly substituted β-lactam derivatives ( Figure 48).…”

Section: Macrolactamization Approachesmentioning

confidence: 99%