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Perrone S.,University of Salento | Salomone A.,University of Bari | Salomone A.,Consorzio Interuniversitario Nazionale Metodologie ocessi Innovativi Of Sintesi Cinmpis | Caroli A.,University of Salento | And 5 more authors.
European Journal of Organic Chemistry | Year: 2014

A direct method to obtain α-alkylidene β-oxo amides by the palladium-catalyzed carbonylation of α-chloro ketones in the presence of aromatic imines has been described. The methodology can be applied to a variety of C-aryl imines bearing N-aryl or N-alkyl substituents. The entire process is highly stereoselective and affords the α-alkylidene β-oxo amides only as (Z) isomers. A mechanistic hypothesis involving an acyl-β-lactam intermediate has also been proposed. © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.


Perrone S.,University of Salento | Cannazza G.,University of Salento | Cannazza G.,University of Modena and Reggio Emilia | Caroli A.,University of Salento | And 5 more authors.
Tetrahedron | Year: 2014

A detailed study on the reactivity of various heterocycles, containing a C-N double bond, with acyl palladium species, generated in situ from allyl or benzyl halides and CO, has been performed. While the cyclic imine 2-methyl-1-pyrroline reacted with acyl-palladium intermediates to give a bicyclic β-lactam, other heterocycles containing a C-N double bond conjugated with a heteroatom (O or N), showed a ring-opening reaction leading to functionalized imides with high structural diversity. Such methodology represents a simple and direct way to prepare structurally complex imides. Moreover, a reaction mechanism, involving cationic intermediates, was also proposed. © 2014.


Perrone S.,University of Salento | Caroli A.,Consorzio Interuniversitario Nazionale Metodologie ocessi Innovativi Of Sintesi Cinmpis | Cannazza G.,University of Modena and Reggio Emilia | Granito C.,University of Salento | And 3 more authors.
Tetrahedron Letters | Year: 2015

A simple and direct method to obtain 3-acyl-4-hydroxy-2-pyranone derivatives by the palladium-catalyzed carbonylation of α-chloroketones has been described. The methodology can be applied to a variety of aromatic and aliphatic ketones to afford valuable products from both a synthetic and a biological point of view. A mechanistic hypothesis involving an acylketene intermediate has also been proposed. © 2015 Elsevier Ltd. All rights reserved.


Perrone S.,University of Salento | Cannazza G.,University of Modena and Reggio Emilia | Caroli A.,University of Salento | Caroli A.,Consorzio Interuniversitario Nazionale Metodologie ocessi Innovativi Of Sintesi Cinmpis | And 3 more authors.
Tetrahedron | Year: 2014

A detailed study on the reactivity of various heterocycles, containing a C-N double bond, with acyl palladium species, generated in situ from allyl or benzyl halides and CO, has been performed. While the cyclic imine 2-methyl-1-pyrroline reacted with acyl-palladium intermediates to give a bicyclic β-lactam, other heterocycles containing a C-N double bond conjugated with a heteroatom (O or N), showed a ringopening reaction leading to functionalized imides with high structural diversity. Such methodology represents a simple and direct way to prepare structurally complex imides. Moreover, a reaction mechanism, involving cationic intermediates, was also proposed. © 2014 Elsevier Ltd. All rights reserved.


Cardona F.,Consorzio Interuniversitario Nazionale Metodologie ocessi Innovativi Of Sintesi Cinmpis | Cardona F.,University of Aveiro | D'Orazio G.,Consorzio Interuniversitario Nazionale Metodologie ocessi Innovativi Of Sintesi Cinmpis | Silva A.M.S.,University of Aveiro | And 2 more authors.
European Journal of Organic Chemistry | Year: 2014

We synthesized fused bicyclic polyfunctional compounds containing a highly hydroxylated pyran ring starting from commercially available methyl glucopyranoside and adopting a RCM annulation approach. The versatile α,β-unsaturated ketone group was introduced on the newly formed ring and, as an example of the potential of these polyfunctionalized building blocks, a tetracyclic compound was synthesized through a Diels-Alder cycloaddition reaction. Bicyclic polyfunctional glycol-fused compounds have been synthesized from commercially available methyl gluco-pyranoside. These molecules, with their high chirality content, presence of an α,β-unsaturated ketone and multiple hydroxyl groups represent useful building blocks for the preparation of complex, optically pure compounds. Copyright © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

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