Enantioselective synthesis of 3a-azido-pyrroloindolines by copper-catalyzed asymmetric dearomative azidation of tryptamines.

Copper-catalyzed asymmetric dearomative azidation of tryptamines using azidobenziodoxolone as an azidating reagent was developed, which affords a variety of 3a-azido-pyrroloindolines in good to high enantioselectivities under mild reaction conditions. The azides could be readily transformed into the corresponding 3a-amino-pyrroloindolines via reduction and 1,2,3-triazole derivatives via a click reaction.

Rhodium-Catalyzed Successive C-H Bond Functionalizations To Synthesize Complex Indenols Bearing a Benzofuran Unit.

An efficient rhodium-catalyzed redox-neutral annulations of N-phenoxyacetamides and ynones via successive double C-H bond activations has been developed. A series of novel and complex indenols bearing a benzofuran unit were generated with moderate to excellent regioselecetivities under mild conditions. Adding N-ethylcyclohexanamine (CyNHEt) could restrict the formation of the mono C-H bond activation byproduct, which is not the intermediate of the reaction demonstrated via the mechanistic investigations.