Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (1): 251-258.DOI: 10.6023/cjoc202305018 Previous Articles     Next Articles



王化坤, 任晓龙, 宣宜宁*()   

  1. 广东药科大学药学院 广州 510006
  • 收稿日期:2023-05-16 修回日期:2023-08-19 发布日期:2023-09-08
  • 基金资助:

Study of the Halide Salt Catalyzed [3+2] Cycloaddition of α,β-Epoxy Carboxylate with Isocyanate

Huakun Wang, Xiaolong Ren, Yining Xuan()   

  1. School of Pharmacy, Guangdong Pharmaceutical University, Guangzhou 510006
  • Received:2023-05-16 Revised:2023-08-19 Published:2023-09-08
  • Contact: *E-mail:
  • Supported by:
    Department of Science and Technology of Guangdong Province(2017A020211027)

The [3+2] cycloaddition reaction of α,β-epoxy carboxylate and isocyanate was investigated. By employing magnesium bromide as a catalyst, efficient synthesis of chiral oxazolidin-2-ones was achieved through aforementioned [3+2] cycloaddition reaction. The reaction exhibited good substrate adaptability. For reactions involving chiral epoxide compounds, the product enantiomeric excess remains good. Furthermore, under basic conditions, taxol C-13 side chain ((2R,3S)-methyl 3-benzamido-2-hydroxy-3-phenylpropanoate) was synthesized via ring-opening reaction of the chiral oxazolidin-2-ones product with an optical purity of up to 97% ee.

Key words: asymmetric synthesis, [3+2] cycloaddition, oxazolidin-2-one, taxol side chain