Iridium-catalyzed C3-selective asymmetric allylation of 7-azaindoles with secondary allylic alcohols

The development of efficient synthetic methods of 7-azaindoles has been desired due to the useful biological activities and physical properties. We report the first example of the iridium-catalyzed C3-selective asymmetric allylation of 7-azaindoles with racemic secondary allylic alcohols to give only branched allylation products in good to high yields with high enantioselectivity (up to >99.5% ee). Allylic alcohols and 7-azaindoles with a variety of functional groups including halogen and heteroaromatic groups are compatible with the reaction conditions. Furthermore, transformations of the obtained allylation products are demonstrated without a significant loss of enantiomeric excess.

Automated summary

The study presents an efficient method catalyzed by iridium for the C3-selective asymmetric allylation of 7-azaindoles with racemic secondary allylic alcohols, yielding only branched allylation products in good to high yields with high enantioselectivity. Various functional groups, including halogen and heteroaromatic groups, are compatible with the reaction conditions. Transformations of the obtained allylation products demonstrate no significant loss of enantiomeric excess.