Stereospecific Aminative Cyclizations Triggered by Intermolecular Aza‐Prilezhaev Alkene Aziridination

Abstract

AbstractUnder acidic reaction conditions (TFA), deprotection of BocNR(OSO2R) reagents triggers intermolecular aminative cyclizations of alkenes equipped with pendant nucleophiles. The processes are predicated on a sequence of stereospecific intermolecular aza‐Prilezhaev aziridination followed by stereospecific SN2‐like opening by the pendant nucleophile. The method offers broad scope with respect to the nucleophile (N‐, O‐ or C‐based), alkene and cyclization mode, allowing the installation of two contiguous stereocenters under operationally simple conditions.