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<p>As the prominence of green chemistry continues to grow, there is an increasing need to explore and develop alternative energy and fuel sources. Renewable biomass is expected to play a pivotal role in this transition, with lactic acid being particularly noteworthy due to its abundance and affordability. Given its prevalence, lactic acid offers a notable opportunity for transformation into high-value-added products. Here, we describe a method for the enantioconvergent substitution of the hydroxy group at the α-position in lactic acid derivatives by a carbon group, thereby streamlining the synthesis of various bioactive compounds. This reaction achieves both C–O bond cleavage and stereochemical C–C bond formation in a one-pot process. Our approach involves a catalyst system based on nickel and relies on two distinct ligands—a chiral bis(imidazoline) and a phthalimide. Investigations into the underlying mechanisms have provided valuable insights into the role of phthalimide in this process.</p>

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Enantioconvergent deoxygenative reductive cross-coupling of lactic acid derivatives

  • 期刊论文

  • 发表日期：

    2025年6月26日

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  • Li-Li Zhang,
  • Yu-Zhong Gao,
  • Ning Wang,
  • Hui Yu,
  • Shou-Jie Shen,
  • Kaining Duanmu,
  • Ze-Peng Yang

摘要

As the prominence of green chemistry continues to grow, there is an increasing need to explore and develop alternative energy and fuel sources. Renewable biomass is expected to play a pivotal role in this transition, with lactic acid being particularly noteworthy due to its abundance and affordability. Given its prevalence, lactic acid offers a notable opportunity for transformation into high-value-added products. Here, we describe a method for the enantioconvergent substitution of the hydroxy group at the α-position in lactic acid derivatives by a carbon group, thereby streamlining the synthesis of various bioactive compounds. This reaction achieves both C–O bond cleavage and stereochemical C–C bond formation in a one-pot process. Our approach involves a catalyst system based on nickel and relies on two distinct ligands—a chiral bis(imidazoline) and a phthalimide. Investigations into the underlying mechanisms have provided valuable insights into the role of phthalimide in this process.