Chiral NHC-catalyzed kinetic resolution of N-aryl
aminomaleimides allowing the synthesis of C–N axially chiral N-aryl aminomaleimides via remote chirality control is presented.
The catalytically generated α,β-unsaturated acylazoliums
from 2-bromoenals underwent selective [3 + 3] annulation with one
of the enantiomers of maleimide to furnish fused-dihydropyridinone
(bearing axial/central chirality, up to 6:1 dr, >99:1 er) leaving
the enantioenriched opposite enantiomer (up to >99:1 er). Studies
on C–N bond rotation barrier and dependence on temperature
are also provided.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.