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Issue 21, 2015
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Diastereoselective synthesis of functionalised carbazoles via a sequential Diels–Alder/ene reaction strategy

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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.

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

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Supplementary files

Article information


Submitted
09 Jan 2015
Accepted
19 Jan 2015
First published
20 Jan 2015

RSC Adv., 2015,5, 16125-16152
Article type
Paper
Author version available

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

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