One-Pot Iridium and Enamine Catalysis

Significance

A one-pot, two-step iridium-catalyzed isomerization of allylic alcohols 1 and subsequent organocatalytic α-alkylation is described. The iridium-catalyzed isomerization makes this process complementary to the more classical strategy of 1,4-addition followed by enamine (or enolate) alkylation to access these synthons. Using a chiral iridium catalyst and a chiral proline-based catalyst highly complex α,β-chiral aldehydes are obtained with great enantiocontrol. Preliminary investigations on a kinetic resolution are also discussed.