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<p>Substituted cyclohexanes are ubiquitous motifs in bioactive molecules. Thermodynamically disfavoured substituted cyclohexane scaffolds can significantly enhance both the biological activity and pharmacokinetic properties of potential drugs. However, achieving stereoselective cross-coupling for the synthesis of these structures with precise kinetic control remains a challenge. Here we present a modular reductive cross-coupling reaction that enables the stereoselective synthesis of thermodynamically disfavoured substituted cyclohexanes, employing simple alkenes as coupling partners. Mechanistically, the exceptional stereochemistry of this reaction is governed by a Heck-type migratory insertion step. The utility of this method is also demonstrated through the concise synthesis of bioactive molecules.</p><p></p>

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A stereoselective reductive cross-coupling reaction with kinetic control

  • 期刊论文

  • 发表日期：

    2025年11月7日

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  • Zhenpeng Shen,
  • Hongjin Shi,
  • Yangyang Li,
  • Xiangyu Zhang,
  • Xiaotian Qi,
  • Guoyin Yin

摘要

Substituted cyclohexanes are ubiquitous motifs in bioactive molecules. Thermodynamically disfavoured substituted cyclohexane scaffolds can significantly enhance both the biological activity and pharmacokinetic properties of potential drugs. However, achieving stereoselective cross-coupling for the synthesis of these structures with precise kinetic control remains a challenge. Here we present a modular reductive cross-coupling reaction that enables the stereoselective synthesis of thermodynamically disfavoured substituted cyclohexanes, employing simple alkenes as coupling partners. Mechanistically, the exceptional stereochemistry of this reaction is governed by a Heck-type migratory insertion step. The utility of this method is also demonstrated through the concise synthesis of bioactive molecules.