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

Abstract

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.

Key words

iron catalysis - boron catalysis - dual catalysis - isoindolones - nucleophilic substitution - neighboring group participation

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