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<p>Amino alcohols are vital in natural products, pharmaceuticals and agrochemicals, and as key building blocks for various applications. Traditional synthesis methods often rely on polar bond retrosynthetic analysis, requiring extensive protecting group manipulations that complicate direct access. Here we show a streamlined approach using a serine-derived chiral carboxylic acid in stereoselective electrocatalytic decarboxylative transformations, enabling efficient access to enantiopure amino alcohols. Unlike conventional strategies, this radical method is both modular and general, offering stereoselective and chemoselective synthesis of diverse substituted amino alcohols. For example, aryl, alkenyl, alkyl and acyl fragments can be coupled efficiently with the serine-derived chiral acid under electrocatalytic decarboxylative conditions. We demonstrate its utility through the rapid synthesis of medicinally important compounds, as well as useful building blocks, highlighting its ability to simplify complex synthetic pathways through entirely different bond disconnections. This electrocatalytic method is robust and scalable, as demonstrated in a 72-gram-scale flow reaction.</p><p></p>

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Stereoselective amino alcohol synthesis via chemoselective electrocatalytic radical cross-couplings

  • 期刊论文

  • 发表日期：

    2025年1月3日

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  • Jiawei Sun,
  • Shuanghu Wang,
  • Kaid C. Harper,
  • Yu Kawamata,
  • Phil S. Baran

摘要

Amino alcohols are vital in natural products, pharmaceuticals and agrochemicals, and as key building blocks for various applications. Traditional synthesis methods often rely on polar bond retrosynthetic analysis, requiring extensive protecting group manipulations that complicate direct access. Here we show a streamlined approach using a serine-derived chiral carboxylic acid in stereoselective electrocatalytic decarboxylative transformations, enabling efficient access to enantiopure amino alcohols. Unlike conventional strategies, this radical method is both modular and general, offering stereoselective and chemoselective synthesis of diverse substituted amino alcohols. For example, aryl, alkenyl, alkyl and acyl fragments can be coupled efficiently with the serine-derived chiral acid under electrocatalytic decarboxylative conditions. We demonstrate its utility through the rapid synthesis of medicinally important compounds, as well as useful building blocks, highlighting its ability to simplify complex synthetic pathways through entirely different bond disconnections. This electrocatalytic method is robust and scalable, as demonstrated in a 72-gram-scale flow reaction.