Title:Autocatalytic Nucleophilic Substitution of Hydroxylactam by Thiophenol: Access to N(acyl), S-acetals
Volume: 3
Issue: 3
Author(s): Fei Qi, Rou Li, Fang Fang and Pengfei Li*
Affiliation:
- Department of Chemistry, South University of Science and Technology of China, 1088 Xueyuan Blvd., Nanshan District, Shenzhen, Guangdong, 518055,China
Keywords:
Catalyst-free, nucleophilic substitution, alcohol, thiophenol, hydroxylactam, N-acylimium ion, N, S-acetal.
Abstract: Background: Catalyst-free nucleophilic substitution between hydroxylactam and thiol was
developed for the construction of N (acyl), S-acetal skeletons.
Methods: The new protocol provides a series of isoindolo-β-carboline-derived N (acyl), S-acetals in
high yields.
Result: The methodology has many advantages, such as catalyst-free, mild reaction conditions, simple
operations, high atom-economy, and water as by-product and so on. The reaction mechanism was
also discussed.
