Diastereoselective Synthesis of Substituted Chromenopyrrolidinones from Amino Acid-Derived Nitriles

Annakaisa Heikinheimo, Martin Nieger, Ari M.P. Koskinen*

*Corresponding author for this work

Research output: Contribution to journalArticleScientificpeer-review

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Abstract

Novel, substituted chromenopyrrolidininones have been synthesized from natural amino acid derivatives through an unprecedented sequence involving a Knoevenagel-Transesterification sequence and an allylative palladium-catalyzed cyclization reaction. The products are nature-inspired heterocycles derived from natural amino acids. The targets could be synthesized with varying degrees of stereoselectivity: racemization is a known issue with amino acids and provided a formidable challenge to our method development, as well. Altogether, six derivatives were synthesized with yields from moderate to good.

Original languageEnglish
Pages (from-to)1512-1518
Number of pages7
JournalSynlett
Volume34
Issue number12
DOIs
Publication statusPublished - 3 Jan 2023
MoE publication typeA1 Journal article-refereed

Keywords

  • 5-endo-Trig
  • Amino acid racemization
  • Chromenopyrrolidine
  • Coumarin
  • Pyrrolidinone

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