Lookup NU author(s): Dr Joe Cowell,
Dr Faye Wolstenhulme,
Dr Paul Waddell,
Dr Mike Probert,
Dr Michael Hall
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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.
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
Online publication date: 20/01/2015
Acceptance date: 19/01/2015
ISSN (electronic): 2046-2069
Publisher: RSC Publications
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