Regio- and Enantioselective Synthesis of Dihydropyrido[1,2-a]indoles via Catalytic Asymmetric Annulative Allylic Alkylation

Xue Wang, Hui-Lin Mao, Yu-Heng Yang, Hong Jiang, Ling-Qi Chen, Shu-Jiang Tu,* Wen-Juan Hao,* Bo Jiang*

A palladium-catalyzed asymmetric annulative allylic alkylation reaction of 2-((1H-indol-2-yl)methyl)malonates with (E)-but-2-ene-1,4-diyl dicarbonates is described, leading to the regio- and enantioselective synthesis of dihydropyrido[1,2-a]indoles with a chiral cyclic allyl stereocenter adjacent to the ring-junction nitrogen atom in moderate to good yields. The salient features of this protocol include mild conditions, broad substrate scope, and good compatibility with substituents as well as high regio- and stereoselectivities, providing a catalytic asymmetric entry to fabricate chiral pyridoindole scaffolds.

J. Org. Chem. 2022,  87(22), 15644-15652; DOI:10.1021/acs.joc.2c01873