Diastereoselective and E/Z-Selective Synthesis of Functionalized Quinolizine Scaffolds via the Dearomative Annulation of 2-Pyridylacetates with Nitroenynes

An organocatalytic Michael/aza-Michael cascade reaction was developed to build the functionalized quinolizine scaffolds in 60-82% yields, excellent diastereoselectivities, and E/Z selectivities. This protocol involves the [3 + 3] annulations of 2-pyridylacetates with nitroenynes through the dearomative strategy in the presence of an organic base under mild conditions. The versatile late-stage derivatizations further demonstrated the synthetic utility of this methodology.

Automated summary

An organocatalytic Michael/aza-Michael cascade reaction was developed for the synthesis of functionalized quinolizine scaffolds with high yields, excellent diastereoselectivity, and E/Z selectivity. This methodology involves the [3 + 3] annulation of 2-pyridylacetates with nitroenynes through dearomative strategy under mild conditions. The versatility of late-stage derivatizations further demonstrates the synthetic utility of this approach.