Stereospecific Aminative Cyclizations Triggered by Intermolecular Aza-Prilezhaev Alkene Aziridination.

Smith, Matthew JS, Tu, Wenbin, Robertson, Craig M and Bower, John F ORCID: 0000-0002-7551-8221 (2023) Stereospecific Aminative Cyclizations Triggered by Intermolecular Aza-Prilezhaev Alkene Aziridination. Angewandte Chemie (International ed. in English), 62 (48). e202312797-.

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Official URL: http://dx.doi.org/10.1002/anie.202312797

Abstract

Under acidic reaction conditions (TFA), deprotection of BocNR(OSO<sub>2</sub> R) 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 S<sub>N</sub> 2-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.

Item Type:	Article
Uncontrolled Keywords:	Amination, Aza-Prilezhaev, Aziridine, Carbocyclization, Heterocyclization
Divisions:	Faculty of Science and Engineering > School of Physical Sciences
Depositing User:	Symplectic Admin
Date Deposited:	20 Nov 2023 15:57
Last Modified:	24 Nov 2023 13:03
DOI:	10.1002/anie.202312797
Open Access URL:	https://doi.org/10.1002/anie.202312797
Related URLs:	Author Publisher
URI:	https://livrepository.liverpool.ac.uk/id/eprint/3176913