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<p>A newly designed chiral guanidine-functionalized bifunctional organocatalyst bearing chloramphenicol base scaffold has been developed and successfully applied in the highly enantioselective alcoholysis of <i>meso</i>-cyclic anhydride. The desired reaction proceeded in excellent enantioselectivities and catalytic activity (up to 97% yield and 99% ee) to afford a series of optically pure chiral hemiesters even at 0.5&#xa0;mol% catalyst loading, which is the first example of catalytic asymmetric alcoholysis promoted by such a low amount of organocatalyst. Furthermore, the scope and limitations of this improved protocol have been demonstrated with more than 20 examples, including the scale-up ability on the gram scale.</p>

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Chiral guanidine-functionalized chloramphenicol base: a novel ultra-low-loading bifunctional organocatalyst for highly enantioselective alcoholysis of meso-cyclic anhydride

  • 期刊论文

  • 发表日期：

    2025年6月11日

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  • Fei Xiong,
  • Huifang Jiang,
  • Jiawei Chen,
  • Yi Gong,
  • Zhenyu Zhang,
  • Heping Xia

摘要

A newly designed chiral guanidine-functionalized bifunctional organocatalyst bearing chloramphenicol base scaffold has been developed and successfully applied in the highly enantioselective alcoholysis of meso-cyclic anhydride. The desired reaction proceeded in excellent enantioselectivities and catalytic activity (up to 97% yield and 99% ee) to afford a series of optically pure chiral hemiesters even at 0.5 mol% catalyst loading, which is the first example of catalytic asymmetric alcoholysis promoted by such a low amount of organocatalyst. Furthermore, the scope and limitations of this improved protocol have been demonstrated with more than 20 examples, including the scale-up ability on the gram scale.