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-.
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 |
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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: | |
URI: | https://livrepository.liverpool.ac.uk/id/eprint/3176913 |