LAUSR

Cycloaromatization reactions of enediyne compounds are renowned for their widespread applications and interesting reactivity characteristics. In the presence of lithium halide and a weak acid, cycloaromatization processes of cyclodeca-1,5-diyn-3-ene can be redirected from the usual formation of a phenyl diradical towards a zwitterionic pathways. We extended the zwitterionic reaction system to other enediyne compounds, and found good applicability in all-carbon systems. While in the case of maleimide based enediynes, only diradical (phenyl-substituted) or anionic (butyl-substituted) cyclization pathway was achieved. Noteworthy, the nucleophilic cyclization of maleimide-based enediyne introduced by bromide ion performed as an unreported C2-C7 cyclization pattern.