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

Jiang Zhu; Jiaji Li; Lianjie Zhang; Shitao Sun; Lu Yang; Jiayue Fu; Hanyang Sun; Maosheng Cheng; Bin Lin; Yongxiang Liu

doi:10.1021/acs.joc.3c00604

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

J Org Chem. 2023 Aug 4;88(15):10586-10598. doi: 10.1021/acs.joc.3c00604. Epub 2023 Jul 14.

Authors

Jiang Zhu^{1

2

3}, Jiaji Li^{1

2

3}, Lianjie Zhang^{1

2

3}, Shitao Sun^{1

2

3}, Lu Yang^{1

2

3}, Jiayue Fu^{1

2

3}, Hanyang Sun^{1

3}, Maosheng Cheng^{1

3}, Bin Lin^{1

2

3}, Yongxiang Liu^{1

2

3}

Affiliations

¹ Key Laboratory of Structure-Based Drug Design and Discovery of Ministry of Education, Shenyang Pharmaceutical University, Shenyang 110016, P. R. China.
² Wuya College of Innovation, Shenyang Pharmaceutical University, Shenyang 110016, P. R. China.
³ Institute of Drug Research in Medicine Capital of China, Benxi 117000, P. R. China.

PMID: 37449800
DOI: 10.1021/acs.joc.3c00604

Abstract

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.