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Synthesis of azabicycles via cascade aza-Prins reactions: accessing the indolizidine and quinolizidine cores

Synthesis of azabicycles via cascade aza-Prins reactions: accessing the indolizidine and quinolizidine cores

Dobbs, Adrian (2015) Synthesis of azabicycles via cascade aza-Prins reactions: accessing the indolizidine and quinolizidine cores. Journal of Organic Chemistry, 80 (20). pp. 9868-9880. ISSN 0022-3263 (Print), 1520-6904 (Online) (doi:10.1021/acs.joc.5b01301)

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Abstract

The first detailed study of intramolecular aza-Prins and aza-silyl-Prins reactions, starting from acyclic materials, are reported. The methods allow rapid and flexible access towards an array of [6,5] and [6,6] aza-bicycles, which form the core skeletons of various alkaloids. Based upon our findings on the aza-Prins and aza-silyl-Prins cyclisations, herein we present simple protocols for the intramolecular preparation of the azabicyclic cores of the indolizidines and quinolizidines using a one pot cascade process of N-acyliminium ion formation followed by aza-Prins cyclisation and either elimination or carbocation trapping. It is possible to introduce a range of different substituents into the heterocycles through a judicial choice of Lewis acid and solvent(s), with halo-, phenyl- and amido- substituted azabicyclic products all being accessed through these highly diastereoselective processes.

Item Type: Article
Uncontrolled Keywords: aza-Prins reaction; aza-silyl-Prins reaction; Lewis acid; cascade cyclisation; aza-bicycle
Subjects: Q Science > QD Chemistry
Faculty / Department / Research Group: Faculty of Engineering & Science > Department of Pharmaceutical, Chemical & Environmental Sciences
Last Modified: 07 Aug 2018 09:19
Selected for GREAT 2016: GREAT a
Selected for GREAT 2017: GREAT a
Selected for GREAT 2018: None
URI: http://gala.gre.ac.uk/id/eprint/13891

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