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<p>A tunable DBU/H<sub>2</sub>O medium was employed to investigate the reaction of isophorone <b>1</b> with a variety of aromatic aldehydes <b>2</b>. One hour mixing of the two components in the medium at room temperature selectively afforded substitution products <b>3</b> through activation of the methyl group γ to the carbonyl functionality of isophorone. When the same mixtures were heated at 60&#xa0;°C for two hours, vinylogous aldol condensation products <b>4</b> were obtained instead. This temperature-dependent reactivity demonstrates the switchable behavior of the DBU/H<sub>2</sub>O system, allowing precise control over the formation of either aldol addition or condensation products. The versatility of this approach was demonstrated by the synthesis of a wide range of derivatives, highlighting the efficiency and selectivity of this organocatalytic method. Structural characterization of the newly formed compounds was achieved by NMR spectroscopy and single-crystal X-ray diffraction, verifying the proposed molecular architectures. Overall, this work presents DBU/H<sub>2</sub>O as a simple, green, and tunable medium to control the selectivity of vinylogous aldol-type reactions in the isophorone system.</p>

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DBU/H2O: a tunable organocatalytic medium to control the reaction of isophorone with aldehydes at vinylogous aldol addition stage

  • 期刊论文

  • 发表日期：

    2026年2月3日

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  • M. Saeed Abaee,
  • Zahra Shaabani,
  • Elaheh Akbarzadeh,
  • Yazdanbakhsh L. Nosood,
  • Mohammad M. Mojtahedi,
  • Abbas Shockravi,
  • Klaus Harms

摘要

A tunable DBU/H2O medium was employed to investigate the reaction of isophorone 1 with a variety of aromatic aldehydes 2. One hour mixing of the two components in the medium at room temperature selectively afforded substitution products 3 through activation of the methyl group γ to the carbonyl functionality of isophorone. When the same mixtures were heated at 60 °C for two hours, vinylogous aldol condensation products 4 were obtained instead. This temperature-dependent reactivity demonstrates the switchable behavior of the DBU/H2O system, allowing precise control over the formation of either aldol addition or condensation products. The versatility of this approach was demonstrated by the synthesis of a wide range of derivatives, highlighting the efficiency and selectivity of this organocatalytic method. Structural characterization of the newly formed compounds was achieved by NMR spectroscopy and single-crystal X-ray diffraction, verifying the proposed molecular architectures. Overall, this work presents DBU/H2O as a simple, green, and tunable medium to control the selectivity of vinylogous aldol-type reactions in the isophorone system.