Synthesis of β-hydroxy-α,β-unsaturated carbonyl compounds via the Morita–Baylis–Hillman reaction of paramagnetic aldehydes

Balázsi, Áron and Kálai, Tamás and Bognár, Balázs (2025) Synthesis of β-hydroxy-α,β-unsaturated carbonyl compounds via the Morita–Baylis–Hillman reaction of paramagnetic aldehydes. MONATSHEFTE FÜR CHEMIE, 156. pp. 457-466. ISSN 0026-9247

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Abstract

To investigate the possibilities of carbon–carbon bond formation in the presence of nitroxides, a novel group of paramagnetic Morita–Baylis–Hillman adducts were synthesized from the reaction starting with fve- and six-membered cyclic nitroxide aldehydes and various activated alkenes in the presence of a base, afording β-hydroxy-α,β-unsaturated carbonyls. These adducts could serve as valuable building blocks in nitroxide chemistry. To extend our study, a Morita–Baylis–Hillman alcohol was converted into an iodine derivative, a key intermediate for nucleophilic substitution, forming new cysteine and alkyne spin labels. Additionally, the paramagnetic acrylate adduct was transformed into a β-ketoester, which could be a starting material for synthesizing new heterocyclic compounds bearing a nitroxide moiety

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