N-Heterocyclic Carbene-Promoted [4+2] Annulation of α-Chloro Hydrazones with α-Chloro Aliphatic Aldehydes to Access Enantioenriched Dihydropyridazinones

An expeditious protocol for the assembly of chiral 4,5-dihydropyridazin-3(2H)-ones from alpha-chloro hydrazones and alpha-chloro aliphatic aldehydes via N-heterocyclic carbene (NHC) catalysis is outlined. These in situ-generated 1,2-diaza-1,3-dienes undergo asymmetric [4+2] annulation with NHC-bound enolates to afford the desired products bearing a stereogenic center at the C4 position. The notable features of this approach include good to excellent enantioselectivities, high functional group tolerance, mild reaction conditions, simple operating procedures, and compatibility with gram-scale synthesis.

Automated summary

An efficient method utilizing N-heterocyclic carbene catalysis for the assembly of chiral 4,5-dihydropyridazin-3(2H)-ones is outlined. The notable features of this approach include excellent enantioselectivities, high functional group tolerance, mild reaction conditions, simple operating procedures, and compatibility with gram-scale synthesis.