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<p>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 five- and six-membered cyclic nitroxide aldehydes and various activated alkenes in the presence of a base, affording <i>β</i>-hydroxy-<i>α</i>,<i>β</i>-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 <i>β</i>-ketoester, which could be a starting material for synthesizing new heterocyclic compounds bearing a nitroxide moiety.</p> Graphical abstract <p></p>

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

  • 期刊论文

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  • 发表日期：

    2025年3月24日

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  • Áron Balázsi,
  • Tamás Kálai,
  • Balázs Bognár

摘要

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 five- and six-membered cyclic nitroxide aldehydes and various activated alkenes in the presence of a base, affording 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.

Graphical abstract