Halodecarboxylation Reaction of 4‐Alkylidene‐β‐lactams

Galletti, Paola; Quintavalla, Arianna; Ventrici, Caterina; Giacomini, Daria

doi:10.1002/ejoc.200900558

Cited by 10 publications

(1 citation statement)

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“…15 The group of Giacomini developed an iododecarboxylation of 4-(carboxyalkylidene)azetidin-2-one to synthesize diiodovinyl-b-lactams. 16 McNelis and co-workers described a ring expansion of 1-iodoethynyl-2-methyl-cyclopentanols with iodine and HTIB to form 2-(diiodomethylidene)-6-methylcyclohexanone. 17 Motivated by the synthetic potential of the possible method, the generality of the present PhIO/Bu 4 NI induced cyclization was then investigated under the established conditions (Table 2).…”

mentioning

confidence: 99%

Hypervalent iodine-mediated regioselective cyclization of acetylenic malonates: facile synthesis of 1-diiodomethylene indane and cyclopentane derivatives

Chen

Fan

2011

Chem. Commun.

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confidence: 99%

Hypervalent iodine-mediated regioselective cyclization of acetylenic malonates: facile synthesis of 1-diiodomethylene indane and cyclopentane derivatives

Chen

Fan

2011

Chem. Commun.

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Elimination Reactions

Birsa

2011

Organic Reaction Mechanisms Series

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The Chemistry of 2‐Azetidinones (β‐Lactams)

Alcaide¹,

Almendros²,

Luna³

2011

Modern Heterocyclic Chemistry

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The large number of recent reports on b-lactam chemistry demonstrates the increasing interest in this important class of compounds. Monocyclic b-lactams frequently serve as precursors for the synthesis of classical bicyclic b-lactam antibiotics. The cyclic 2-azetidinone skeleton has been extensively used as a template on which to build the heterocyclic structure fused to the four-membered ring, using the chirality and functionalization of the b-lactam nucleus as a stereocontrolling element. The discovery of nonclassical b-lactam antibiotics, such as monobactams and nocardicins, coupled with ever-growing new applications such as enzyme inhibition has triggered a renewed interest in the building of new monocyclic b-lactam derivatives. Besides the utility of b-lactams as biologically active agents, they are used as intermediates in a-and b-amino acid synthesis, as well as building blocks for alkaloids, heterocycles, taxoids and other types of compounds of biological and medicinal interest. Physicochemical Data Computational ChemistryTheoretical studies show that b-lactams are weaker bases, in the gas phase, than acyclic amides [1]. The attenuation of basicity upon cyclization is stronger than that found for cyclic ketones of similar size due to the existence of a negative hyperconjugation effect that is present in b-lactams but not in cyclic ketones. Ab initio calculations indicate that both b-lactams and acyclic amides are oxygen bases, but the gap between the oxygen and nitrogen intrinsic basicities is much smaller in the former due to the aforementioned cyclization effects. This decrease of the oxygen Modern Heterocyclic Chemistry, First Edition. Edited

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Halodecarboxylation Reaction of 4‐Alkylidene‐β‐lactams

Cited by 10 publications

References 19 publications

Hypervalent iodine-mediated regioselective cyclization of acetylenic malonates: facile synthesis of 1-diiodomethylene indane and cyclopentane derivatives

Hypervalent iodine-mediated regioselective cyclization of acetylenic malonates: facile synthesis of 1-diiodomethylene indane and cyclopentane derivatives

Elimination Reactions

The Chemistry of 2‐Azetidinones (β‐Lactams)

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