Reactions of macrocyclic rhodium carbenoids: regioselective synthesis of indol-3-yl macrocyclic lactones and cryptands

A wide variety of new macrocyclic diazocarbonyl compounds with various spacers was synthesized. Macrocyclic rhodium(II) carbenoid insertion with various substituted indoles was performed to afford regioselectively, indol-3-yl macrocyclic di- or tetralactones (C3-alkylation). Double carbenoid insertion was also performed to afford indolyl cryptand molecules.

Graphical abstractA wide variety of new macrocyclic diazocarbonyl compounds was synthesized and their rhodium(II) acetate catalyzed carbenoid insertion reaction with substituted indoles afforded regioselectively indol-3-yl macrocyclic di- or tetralactones or indolyl cryptand molecules.Download full-size image