Catalysis

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

Authors

Abstract

We report a method for the synthesis of chiral vicinal chlo-roamines via asymmetric protonation of catalytically gener-ated prochiral chloroenamines using chiral Brønsted acids. The process is highly enantioselective, with the origin of asymmetry and catalyst substituent effects elucidated by DFT calculations. We show the utility of the method as an approach to the synthesis of a broad range of heterocycle-substituted aziridines by treatment of the chloroamines with base in a one-pot process, as well as the utility of the process to allow access to vicinal diamines.

Content

Thumbnail image of Manuscript FINAL.pdf

Supplementary material

Thumbnail image of Supporting Information (characterisation data).pdf
Supporting information (characterisation data)
Supporting information file (characterisation data)
Thumbnail image of Supporting Information (NMR spectra).pdf
Supporting information file (NMR spectra)
Supporting information file (NMR spectra)
Thumbnail image of Supporting Information (coordinates).pdf
Supporting information file (coordinates)
Supporting information file (coordinates)