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Catalytic Asymmetric γ-Lactam Synthesis from Enolisable Anhydrides and Imines.

Aarón Gutiérrez CollarCristina TrujilloBruce Lockett-WaltersBrendan TwamleyStephen J Connon
Published in: Chemistry (Weinheim an der Bergstrasse, Germany) (2019)
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.
Keyphrases
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