Toggle Main Menu Toggle Search

Open Access padlockePrints

Diastereoselective synthesis of functionalised carbazoles via a sequential Diels-Alder/ene reaction strategy

Lookup NU author(s): Dr Joe Cowell, Matokah Abualnaja, Stephanie Morton, Dr Faye Wolstenhulme, Dr Paul Waddell, Dr Mike Probert, Dr Michael Hall

Downloads

Full text for this publication is not currently held within this repository. Alternative links are provided below where available.


Abstract

An operationally simple one-pot, three-component, diastereoselective synthesis of saturated carbazoles and related pyridazino[3,4-b]indoles, based on two sequential intermolecular pericyclic reactions, is described. The reaction sequence involves an intermolecular Diels-Alder (D-A) reaction of a 3-vinyl-1H-indole, containing an electron withdrawing N-protecting group, with a suitable dienophile. Due to the electron withdrawing nature of the N-protecting group the resultant D-A cycloadducts are sufficiently stabilised to allow for a subsequent in situ diastereospecific intermolecular ene reaction to take place with an added enophile, generating functionalised carbazoles with relative stereocontrol of up to four stereocentres.


Publication metadata

Author(s): Cowell J, Abualnaja M, Morton S, Linder R, Buckingham F, Waddell PG, Probert MR, Hall MJ

Publication type: Article

Publication status: Published

Journal: RSC Advances

Year: 2015

Volume: 5

Issue: 21

Pages: 16125-16152

Online publication date: 20/01/2015

Acceptance date: 19/01/2015

ISSN (electronic): 2046-2069

Publisher: RSC Publications

URL: http://dx.doi.org/10.1039/C5RA00499C

DOI: 10.1039/C5RA00499C


Altmetrics

Altmetrics provided by Altmetric


Actions

Find at Newcastle University icon    Link to this publication


Share