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Pd-Catalyzed Asymmetric Allylic Substitution Cascade of But-2-ene-1,4-diyl Dimethyl Dicarbonate for the Synthesis of Chiral 2,3-Dihydrofurans.

Hao LiuZhenliang SunKai XuYan ZhengDelong LiuWanbin Zhang
Published in: Organic letters (2020)
Herein an efficient Pd-catalyzed asymmetric allylic substitution cascade of both (E)- and (Z)-but-2-ene-1,4-diyl dimethyl dicarbonates with α-substituted cyano ketones is described for the preparation of chiral 2,3-dihydrofurans in up to 97% yield with 98% ee. A suggested steric control process has been proposed to illustrate the differences in enantioselectivity between the reactions of (E)- and (Z)-allyl substrates. The cascade reaction could be conducted on a gram-scale, and the resulting product allows for several transformations.
Keyphrases
  • room temperature
  • ionic liquid
  • capillary electrophoresis
  • gram negative
  • molecular docking
  • solid state
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  • high resolution
  • multidrug resistant
  • molecular dynamics simulations
  • liquid chromatography