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Lookup NU author(s): Matokah Abualnaja, Dr Joe Cowell, John Jolliffe, Dr Corinne Wills, Dr Paul Waddell, Professor William Clegg, Dr Michael HallORCiD
This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License (CC BY-NC-ND).
Herein we present a rearomative diastereoselective etherification/amination reaction of 2,3,9,9a-tetrahydro-1H-carbazoles, themselves accessible via the Diels-Alder reaction of N-protected 3-vinyl-1H-indoles. We have developed a one-pot rearomative bromination/nucleophilic substitution reaction sequence employing both O- and N-centred nucleophiles, inverting the typical reactivity of 2,3,9,9a-tetrahydro-1H-carbazoles at the 4-position. Alcohols or secondary amines can be incorporated allowing access to the corresponding 4-substituted-2,3,4,9-tetrahydro-1H-carbazoles, the diastereoselectivity of the reaction being controlled by the nature of the nucleophile and the reaction conditions.
Author(s): Abualnaja M, Cowell J, Jolliffe JD, Wills C, Waddell PG, Clegg W, Hall MJ
Publication type: Article
Publication status: Published
Journal: Tetrahedron
Year: 2021
Volume: 89
Print publication date: 04/06/2021
Online publication date: 20/04/2021
Acceptance date: 06/04/2021
Date deposited: 06/04/2021
ISSN (electronic): 0040-4020
Publisher: Elsevier
URL: https://doi.org/10.1016/j.tet.2021.132144
DOI: 10.1016/j.tet.2021.132144
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