Asymmetric synthesis of heterocyclic chloroamines and aziridines by enantioselective protonation of catalytically generated enamines

Liam McLean, Matthew Ashford, Jamie Fyfe, Alexandra Martha Zoya Slawin, Andrew G. Leach, Allan J. B. Watson*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

3 Citations (Scopus)
8 Downloads (Pure)

Abstract

We report a method for the synthesis of chiral vicinal chloroamines via asymmetric protonation of catalytically generatedprochiral chloroenamines using chiral Brønsted acids. The processis highly enantioselective, with the origin of asymmetry and catalystsubstituent effects elucidated by DFT calculations. We show theutility of the method as an approach to the synthesis of a broadrange of heterocycle-substituted aziridines by treatment of thechloroamines with base in a one-pot process, as well as the utility ofthe process to allow access to vicinal diamines.
Original languageEnglish
Article numbere202200060
Number of pages6
JournalChemistry - A European Journal
Volume28
Issue number16
Early online date23 Feb 2022
DOIs
Publication statusPublished - 16 Mar 2022

Keywords

  • Asymmetric catalysis
  • Aziridine
  • Bronstead acid
  • Chloroamine
  • Heterocycles

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