Ir-Catalyzed cyclization of α,ω-dienes with an N-methyl group via two C-H activation steps.

Iridium-catalyzed sp3 C-H alkylation of an N-methyl group with 1,5- and 1,6-dienes proceeded to give five- and six-membered carbocyclic compounds, respectively, in high yields. The reaction involves intermolecular alkylation of the N-methyl group with a vinyl moiety and subsequent intramolecular cyclization at the ß-position of the initially formed alkylated intermediate. The reaction using a chiral bidentate phosphine ligand enabled the asymmetric synthesis of the cyclic compounds.

Iridium-catalyzed stereoselective [3+2] annulation of α-oxocarboxylic acids with 1,3-dienes.

The stereoselective annulation of α-oxocarboxylic acids with 1,3-dienes proceeded in the presence of a hydroxoiridium catalyst to give α-hydroxy-γ-lactones in good yields with high 3,5-trans relative stereochemistry. The use of a chiral diene ligand for a cationic iridium complex enabled asymmetric annulation with high enantioselectivity.