Copper-catalyzed aerobic oxidative radical alkoxycyclization of tryptamines to access 3-alkoxypyrroloindolines

We report a copper-catalyzed alkoxycyclization of tryptamine derivatives with O-2 as the sole oxidant, leading to a variety of C3a-alkoxypyrroloindolines in good yields with high diastereoselectivities. This reaction involves an interesting double catalytic cycle in which copper-catalyzed carboamination cyclization is favored to form the C-3 radical pyrrolidinoindoline intermediate, then a copper-catalytic radical alkoxylation reaction proceeds smoothly.

Automated summary

A copper-catalyzed alkoxycyclization of tryptamine derivatives with O-2 as the oxidant has been developed, providing a variety of C3a-alkoxypyrroloindolines in good yields with high diastereoselectivities. The reaction involves a double catalytic cycle with copper-catalyzed carboamination cyclization followed by a copper-catalyzed radical alkoxylation reaction.