Stereoselective Synthesis of Pyrroloisoindolone and Pyridoisoindolone via aza-Prins Cyclization of Endocyclic <i>N</i>‑Acyliminium Ions

Abstract

A simple methodology has been developed for the synthesis of substituted pyrroloisoindolone and pyridoisoindolone via aza-Prins cyclization of endocyclic <i>N</i>-acyliminium ions, which are derived from the triflic acid treatment of regioselectively reduced <i>N</i>-homopropargyl imides in excellent yields. The reaction is highly diastereoselective, and only one diastereoisomer is formed during the reaction. The methodology can be utilized for the synthesis of pyrimidoisoindole