Stereospecific Aminative Cyclizations Triggered by Intermolecular Aza-Prilezhaev Alkene Aziridination

Under 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. Under 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 opening by the pendant nucleophile.+image

Automated summary

This article introduces an aminative cyclization reaction under acidic conditions, which is triggered by the deprotection of BocNR(OSO2R) reagents and carried out on alkenes equipped with pendant nucleophiles. The method offers flexibility in terms of choosing nucleophiles, alkenes, and cyclization modes, and enables the construction of consecutive stereocenters under operationally simple conditions.