A Stereospecific Alkene 1,2-Aminofunctionalization Platform for the Assembly of Complex Nitrogen-Containing Ring Systems

Zhu, Yuxiang, Smith, Matthew JS, Tu, Wenbin and Bower, John F ORCID: 0000-0002-7551-8221 (2023) A Stereospecific Alkene 1,2-Aminofunctionalization Platform for the Assembly of Complex Nitrogen-Containing Ring Systems. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 62 (16). e202301262-.

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Official URL: http://dx.doi.org/10.1002/anie.202301262

Abstract

TFA promoted deprotection of O-Ts activated N-Boc hydroxylamines triggers aminofunctionalization-based polycyclizations of tethered alkenes. The processes involve intramolecular stereospecific aza-Prilezhaev alkene aziridination in advance of stereospecific C-N cleavage by a pendant nucleophile. Using this approach, a wide range of fully intramolecular alkene anti-1,2-difunctionalizations can be achieved, including diaminations, amino-oxygenations and amino-arylations. Trends associated with the regioselectivity of the C-N cleavage step are outlined. The method provides a broad and predictable platform for accessing diverse C(sp<sup>3</sup> )-rich polyheterocycles of relevance to medicinal chemistry.

Item Type:	Article
Uncontrolled Keywords:	Alkenes, Aminofunctionalization, Aziridines, Cascade Reactions, Stereospecificity
Divisions:	Faculty of Science and Engineering > School of Physical Sciences
Depositing User:	Symplectic Admin
Date Deposited:	31 Mar 2023 08:14
Last Modified:	14 Apr 2023 03:33
DOI:	10.1002/anie.202301262
Open Access URL:	https://doi.org/10.1002/anie.202301262
Related URLs:	Author Publisher
URI:	https://livrepository.liverpool.ac.uk/id/eprint/3169373