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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Modular Synthesis of Enantioenriched α-Chiral Homoallylic Amidines Enabled by Relay Ir/Cu Catalysis
Ting-Peng Li1, Ren-Sha Li1, Wei Hu1
1College of Chemistry and Materials Science, Sichuan Normal University, Chengdu, Sichuan 610068, China.
Abstract:
The cascade of Ir-catalyzed enantioselective allylic amination and Cu-catalyzed alkyne-azide cycloaddition was designed for the asymmetric synthesis of homoallylic amidines. The nucleophilic addition of an in situ-generated enantioenriched tertiary allylamine to a ketenimine intermediate triggers a rapid and stereospecific zwitterionic aza-Claisen rearrangement in a 1,3-chiral transfer manner. The approach allows modular access to enantioenriched α-chiral homoallylic amidines in high yields with a high level of enantiomeric purity.
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