Ag(I)/PPh3-catalyzed diastereoselective syntheses of spiro[indole-3,4'-piperidine] derivatives via cycloisomerizations of tryptamine-ynamides

Yanyu Chen; Zhaobo Wang; Wutong Zhao; Shitao Sun; Lu Yang; Junpeng Zhang; Di Zhang; Maosheng Cheng; Bin Lin; Yongxiang Liu

doi:10.1039/d1cc07298f

Ag(I)/PPh₃-catalyzed diastereoselective syntheses of spiro[indole-3,4'-piperidine] derivatives via cycloisomerizations of tryptamine-ynamides

Chem Commun (Camb). 2022 Mar 1;58(18):3051-3054. doi: 10.1039/d1cc07298f.

Authors

Yanyu Chen^{1

2

3}, Zhaobo Wang^{1

2

3}, Wutong Zhao¹, Shitao Sun^{1

3}, Lu Yang^{1

2

3}, Junpeng Zhang^{1

3}, Di Zhang^{1

3}, Maosheng Cheng^{1

3}, Bin Lin^{1

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. yongxiang.liu@syphu.edu.cn.
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: 35165679
DOI: 10.1039/d1cc07298f

Abstract

A Ag(I)/PPh₃-catalyzed chelation-controlled cycloisomerization of tryptamine-ynamide was developed to access the spiro[indole-3,4'-piperidine] scaffold in a racemic and diastereoselective manner. The diastereoselective products were achieved by a chiron approach. Density functional theory (DFT) calculations indicated that strong non-covalent effects between the substrate and catalyst/ligand complex stabilized the spiroindoleninium intermediate via cation-π-π interactions.