Gold(I)-Catalyzed Substitution-Controlled Syntheses of Spiro[indoline-3,3 ' -pyrrolidine] and Spiro[indoline-3,3 ' -piperidine] Derivatives.

Spiro[indoline-3,3 ' -pyrrolidine] and spiro[indoline-3,3 ' -piperidine] derivatives were synthesized in a substitution-controlled manner under the catalysis of cationic gold(I) species in the presence of Hantzsch ester (HEH). The optimal reaction condition was determined by screening, and the functional group tolerances of these two pathways were examined by readily synthetic substrates. The endo and exo selectivities of these cyclizations were elucidated by density functional theory calculations, and a plausible mechanism for these transformations was proposed.