Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 25, Issue 30, Pages 7275-7279Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201901028
Keywords
cyclic anhydrides; cycloadditions; DFT; imines; lactams
Categories
Funding
- Science Foundation Ireland [SFI-12-IA-1645]
Ask authors/readers for more resources
An anion-binding approach to the problem of preparing enantioenriched gamma-lactams from enolisable anhydrides and imines is reported. A simple bisurea catalyst promotes the cycloaddition between alpha-aryl succinic anhydrides and either PMP- or benzhydryl-protected aldimines to provide gamma-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.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available