Iridium-Catalyzed Regioselective Hydroalkynylation of Internal Alkenes Directed by an Oxime

We report here an iridium-catalyzed hydroalkynylation of allylic alcohols protected by an oxime group. Catalytic alkynylation occurs exclusively at the distal position of the alkene. This method generates gamma-alkynyl alcohol oximes directly from internal alkenes and terminal alkynes. The oxime group can be readily removed to afford a free alcohol, thus providing an indirect route for the catalytic hydroalkynylation of allylic alcohols.

Automated summary

The method involves iridium-catalyzed hydroalkynylation of allylic alcohols protected by an oxime group, generating gamma-alkynyl alcohol oximes directly. The oxime group can be easily removed to obtain free alcohols, offering an indirect route for the catalytic hydroalkynylation of allylic alcohols.