Stereoselective Synthesis of 1,n-Dicarbonyl Compounds Through Palladium-Catalyzed Ring Opening/Isomerization of Densely Substituted Cyclopropanols

Charlotte S. Teschers, Anthony Cohen, Ilan Marek

Research output: Contribution to journalArticlepeer-review

Abstract

We report a highly diastereoselective protocol for the synthesis of 1,4- and 1,5-dicarbonyl compounds from densely substituted cyclopropanols. The methodology involves a palladium-catalyzed ring opening reaction followed by a “metal-walk” and oxidation of a remote hydroxyl group. The methodology represents a new application of cyclopropanols as initiation sites for chain walking remote functionalization. Importantly, this approach provides a straightforward access to highly valuable succinaldehyde derivatives bearing vicinal quaternary and tertiary stereocenters as single diastereomers.

Original languageEnglish
JournalAngewandte Chemie - International Edition
DOIs
StateAccepted/In press - 2024

Keywords

  • chain walking
  • cyclopropanols
  • homoenolates
  • palladium catalysis
  • stereoselective synthesis

All Science Journal Classification (ASJC) codes

  • Catalysis
  • General Chemistry

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