O-Allylated Pudovik and Passerini Adducts as Versatile Scaffolds for Product Diversification

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Metal-Free Addition of Boronic Acids to Silylnitronates

International audienceWe report for the first time a metal-free addition of boronic acids to silylnitronates to afford oxime derivatives through aryl transfer on the carbon nitrogen double bond. A reaction mechanism has been proposed in relation with a DFT study on the key aryl transfer. This arylation process is effective for cycloalkenyl nitro derivatives leading to oximes that may be oxidatively converted into 3-arylisoxazole derivatives

A Passerini/Tsuji-Trost access to dienamide derivatives

International audienceThe Passerini reaction of α, β-unsaturated aldehydes affords allylic acetates which may be involved in Tsuji-Trost elimations towards conjugated dienamides. The interest of these 2,4-dienamides has been demonstrated in several TiCl4 triggered Diels-Alder reactions with N-phenylmaleimide

Straightforward access to complex isoindolinones from the Ugi reaction of o -nitrobenzoic acid derivatives

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Palladium triggered diene formation from nitro allylic compounds: a versatile entry into naphthalene derivatives

International audienceNitro allylic derivatives were converted into dienes through the elimination of the nitro group under basic treatment, in the presence of a palladium catalyst. This reaction probably involves the formation of a palladium π-allyl complex followed by a base-promoted β-hydride elimination. This reaction, combined with the condensation of ketones with nitromethane and the functionalization of the resulting nitrocycloalkenes, constitutes a very powerful synthetic tool for the formation of dienes. Particular attention has been brought to the application of this methodology to the formation of 1-substituted naphthalenes from 1-tetralone