Catalytic Asymmetric γ-Lactam Synthesis from Enolisable Anhydrides and Imines

Aarón Gutiérrez Collar, Cristina Trujillo, Bruce Lockett-Walters, Brendan Twamley, Stephen J. Connon*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

An anion-binding approach to the problem of preparing enantioenriched γ-lactams from enolisable anhydrides and imines is reported. A simple bisurea catalyst promotes the cycloaddition between α-aryl succinic anhydrides and either PMP- or benzhydryl-protected aldimines to provide γ-lactams with two contiguous stereocentres (one quaternary) with complete diastereocontrol and high to excellent enantioselectivity for the first time. A DFT study has provided insight into the catalyst mode of action and the origins of the observed stereocontrol.

Original languageEnglish
Pages (from-to)7275-7279
Number of pages5
JournalChemistry - A European Journal
Volume25
Issue number30
Early online date2 May 2019
DOIs
Publication statusPublished - 28 May 2019

Keywords

  • cyclic anhydrides
  • cycloadditions
  • DFT
  • imines
  • lactams

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