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<p>A new facile method for the preparation of mono- and di-malonates of sterically hindered cage alcohols (1-adamantanol, its derivatives, and (–)-borneol) has been developed. The described reaction was successfully scaled up to the gram level. It was found that when performed in refluxing toluene with a Dean-Stark apparatus, the reaction proceeds efficiently without the need for a catalyst. Additionally, a method for separating diadamantyl (or dibornyl) malonates from the corresponding adamantyl (or bornyl) methyl (or ethyl) malonates by column chromatography was established. The synthesized compounds are suitable for the selective modification of malonic esters.</p> Graphical abstract <p><i>Synopsis</i>. This study reports a catalyst-free, one-pot transesterification of dimethyl malonate with bulky cage alcohols in refluxing toluene, demonstrating a highly selective route to complex esters that is effective on a gram-scale.</p>

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Facile synthesis of adamantyl and bornyl malonates via catalyst-free transesterification

  • 期刊论文

  • 发表日期：

    2026年3月2日

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  • Vladimir Burmistrov,
  • Daria Zapravdina,
  • Ilya Yakushev,
  • Anna Maximova,
  • Artemiy Nichugovskiy

摘要

A new facile method for the preparation of mono- and di-malonates of sterically hindered cage alcohols (1-adamantanol, its derivatives, and (–)-borneol) has been developed. The described reaction was successfully scaled up to the gram level. It was found that when performed in refluxing toluene with a Dean-Stark apparatus, the reaction proceeds efficiently without the need for a catalyst. Additionally, a method for separating diadamantyl (or dibornyl) malonates from the corresponding adamantyl (or bornyl) methyl (or ethyl) malonates by column chromatography was established. The synthesized compounds are suitable for the selective modification of malonic esters.

Graphical abstract

Synopsis. This study reports a catalyst-free, one-pot transesterification of dimethyl malonate with bulky cage alcohols in refluxing toluene, demonstrating a highly selective route to complex esters that is effective on a gram-scale.