ArticleChemistry (Weinheim an der Bergstrasse, Germany)2026
Organocatalytic Formal (3+2+1)-Cycloaddition of Allenoates, Michael Acceptors, and Carbaldehydes.
Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2026. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.
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Abstract
Employing secondary amines as covalently interacting Lewis basic organocatalysts allows for the activation of electron-deficient allenes (allenoates) for unprecedented formal (3+2+1)-cycloadditions with Michael acceptors and aromatic carbaldehydes. This strategy is proposed to proceed via nucleophilic addition of the catalyst to the allenoate's β-carbon first, followed by γ-addition to the Michael acceptor, a subsequent aldol-type step, and the final ring closure and catalyst liberation. Hereby, direct access to various highly functionalized spirocyclic cyclohexanone-derivatives (17 examples) in good to excellent yields (up to 98%) and a first proof-of-concept for an asymmetric variant (around 75:25 er) by using chiral secondary amine catalysts has been obtained as well.
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