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Synthesis of Cyclic β-Amino Acid Derivatives by Desymmetrization and Lossen Rearrangement of N -Sulfoxy Meso-Succinimides.

Dylan HardeeChan Woo HuhJeffrey Aube
Published in: The Journal of organic chemistry (2024)
Bifunctional thiourea-based organocatalysts facilitate an enantioselective desymmetrization and Lossen rearrangement cascade reaction of N -sulfoxy meso -succinimides, resulting in the synthesis of cyclic β-amino acid derivatives. This catalytic system was optimized for bicyclic and tricyclic succinimide substrates affording yields from 61-91% and up to 96:4 er. This reaction proceeds via the group selective addition of the primary alcohol nucleophile to an enantiotopic carbonyl group with sequential rearrangement of the intermediate O -sulfonyl hydroxamate ester.
Keyphrases
  • amino acid
  • structure activity relationship
  • estrogen receptor
  • alcohol consumption
  • endoplasmic reticulum
  • breast cancer cells
  • metal organic framework