Jump to main content
Jump to site search

Issue 21, 2015
Previous Article Next Article

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

Author affiliations

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.

Graphical abstract: Diastereoselective synthesis of functionalised carbazoles via a sequential Diels–Alder/ene reaction strategy

Back to tab navigation

Supplementary files

Publication details

The article was received on 09 Jan 2015, accepted on 19 Jan 2015 and first published on 20 Jan 2015


Article type: Paper
DOI: 10.1039/C5RA00499C
Author version
available:
Download author version (PDF)
RSC Adv., 2015,5, 16125-16152

  •   Request permissions

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

    J. Cowell, M. Abualnaja, S. Morton, R. Linder, F. Buckingham, P. G. Waddell, M. R. Probert and M. J. Hall, RSC Adv., 2015, 5, 16125
    DOI: 10.1039/C5RA00499C

Search articles by author

Spotlight

Advertisements