Scholarlink

<p>Chiral amino acids are essential building blocks in asymmetric synthesis and drug discovery, yet their efficient preparation from racemic mixtures remains challenging. Here we show that a rationally designed phosphine oxide catalyst derived from <i>L</i>-pyroglutaminol enables the highly efficient kinetic resolution of racemic amino acids under mild conditions. Using <i>L</i>-pyroglutaminol as the esterification reagent, this catalytic system delivers a broad range of chiral esters and recovered amino acids with excellent stereoselectivities (s &gt; 1057). Mechanistic studies suggest that the superior stereocontrol arises from a cooperative double hydrogen-bonding interaction between the catalyst and the pyroglutaminol core. This work provides a practical and scalable approach to enantioenriched amino acids, highlighting the potential of dual chiral cooperative catalysis in asymmetric synthesis.</p>

错误：搜索内容不能为空，请输入英文关键词
错误：关键词超出字数限制，请精简
高级检索

Kinetic resolution of amino acids by phosphine oxide catalyzed enantioselective esterification

  • 期刊论文

  • 出版模式：

    开放获取

  • 发表日期：

    2026年4月13日

查看全文
  • Ji-Wei Ren,
  • Jing-Hui Sun,
  • Ke-Hang Li,
  • Mu-Ran Lin,
  • Jin-Lan Zeng,
  • Xiao-Mei Ai

摘要

Chiral amino acids are essential building blocks in asymmetric synthesis and drug discovery, yet their efficient preparation from racemic mixtures remains challenging. Here we show that a rationally designed phosphine oxide catalyst derived from L-pyroglutaminol enables the highly efficient kinetic resolution of racemic amino acids under mild conditions. Using L-pyroglutaminol as the esterification reagent, this catalytic system delivers a broad range of chiral esters and recovered amino acids with excellent stereoselectivities (s > 1057). Mechanistic studies suggest that the superior stereocontrol arises from a cooperative double hydrogen-bonding interaction between the catalyst and the pyroglutaminol core. This work provides a practical and scalable approach to enantioenriched amino acids, highlighting the potential of dual chiral cooperative catalysis in asymmetric synthesis.