Catalyst-Free ?-Allylation of Dihydroisoquinolines with Morita-Baylis-Hillman Carbonates and Its Applications in the Construction of Benzo[a]quinolizidines

In this work, a mild and efficient catalyst-free alpha-allylation of 3,4-dihydroisoquinoline imines with Morita-Baylis- Hillman (MBH) carbonates was reported. The scopes of 3,4-dihydroisoquinolines and MBH carbonates as well as gram-scale synthesis were investigated, and densely functionalized adducts were obtained in moderate to good yields. The synthetic utility of these versatile synthons was further demonstrated by the facile synthesis of diverse benzo[a]quinolizidine skeletons.

Automated summary

A mild and efficient catalyst-free alpha-allylation of 3,4-dihydroisoquinoline imines with Morita-Baylis-Hillman (MBH) carbonates was successfully achieved. The study includes the investigation of the scope of 3,4-dihydroisoquinolines and MBH carbonates, as well as gram-scale synthesis. Densely functionalized adducts were obtained in moderate to good yields, demonstrating the synthetic utility of these versatile synthons.