Organic chemistry

Combinatorial chemistry

Stereochemistry

Enantioselective synthesis

Catalysis

Chemistry

Carbene

Isatin

Oxindole

Annulation

The Journal of Organic Chemistry

Herein, we report an enantioselective synthesis of azepinones via the N-heterocyclic carbene (NHC) catalyzed [3+4] annulation reaction of isatin-derived enals and aurone-derived azadienes. The corresponding spirocyclic oxindole-benzofuroazepinones were obtained in good yields, with excellent diastereo- and enantioselectivities. The resulted azepinones were evaluated for their in vitro cytotoxic activities against six human tumor cell lines, with two compounds showing significant inhibitory activity comparable with that of cisplatin.

Enantioselective N-Heterocyclic Carbene-Catalyzed Synthesis of Spirocyclic Oxindole-benzofuroazepinones