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Expanding the Protecting Group Scope for the Carbonyl Olefin Metathesis Approach to 2,5-Dihydropyrroles.

Fabian HuckLorenzo CattiGian Lino ReberKonrad Tiefenbacher
Published in: The Journal of organic chemistry (2021)
Chiral pyrrolidine derivatives are important building blocks for natural product synthesis. Carbonyl olefin metathesis has recently emerged as a powerful tool for the construction of such building blocks from chiral amino acid derivatives. Here, we demonstrate that the supramolecular resorcinarene catalyst enables access to chiral 2,5-dihydropyrroles under Brønsted acid catalysis. Moreover, this catalytic system even tolerated Lewis-basic-protecting groups like mesylates that are not compatible with alternative catalysts. As expected for conversion inside a closed cavity, the product yield and selectivity depended on the size of the substrates.
Keyphrases
  • ionic liquid
  • capillary electrophoresis
  • amino acid
  • highly efficient
  • room temperature
  • metal organic framework
  • mass spectrometry
  • structure activity relationship
  • visible light
  • reduced graphene oxide
  • carbon dioxide