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Diastereoselective Rearomative Etherifications and Aminations of 2,3,9,9a-Tetrahydro-1H-carbazoles

Lookup NU author(s): Matokah Abualnaja, Dr Joe Cowell, John Jolliffe, Dr Corinne Wills, Dr Paul Waddell, Emeritus Professor Bill CleggORCiD, Dr Michael HallORCiD

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Abstract

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.

Publication metadata

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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