Autocatalytic Nucleophilic Substitution of Hydroxylactam by Thiophenol: Access to N(acyl), S-acetals

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-beta-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.