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Catalytic Direct Nucleophilic Substitution of Primary Morita–Baylis­–Hillman Adducts and Application to the Straightforward Synthesis of Dihydroisoindolones
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Catalytic Direct Nucleophilic Substitution of Primary Morita–Baylis­–Hillman Adducts and Application to the Straightforward Synthesis of Dihydroisoindolones

Marwa Ayadi, Pierre Mpawenayo, Farhat Rezgui, Eric Leclerc, Emmanuel Vrancken et Jean-Marc Campagne
Synthesis: Journal of Synthetic Organic Chemistry, Vol.50(2), pp.pp. 1166-1174
14/11/2017
DOI: https://doi.org/10.1055/s-0036-1589131

Résumé

neighboring group participation nucleophilic substitution isoindolones dual catalysis boron catalysis iron catalysis
An interesting γ-carbonyl effect permits the dual iron/boron-catalyzed direct nucleophilic substitution of functionalized primary allylic­ alcohols with a large variety of nucleophiles. The resulting substitution products are useful synthetic platforms for heterocycle synthesis, as illustrated in a ready access to tetrahydroisoindol-4-ones.

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