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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 WolstenhulmeORCiD, Dr Paul Waddell, Professor Mike ProbertORCiD, Dr Michael HallORCiD

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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

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