Stereoselective double Friedel-Crafts alkylation of indoles with divinyl ketones

Andrew C Silvanus, Stephen J Heffernan, D J Liptrot, Gabriele Kociok-Kohn, B I Andrews, David R Carbery

Research output: Contribution to journalArticle

39 Citations (Scopus)

Abstract

A tandem double Friedel-Crafts reaction of indoles and nonsymmetrical divinyl ketones has been achieved. The tandem reaction forms complex [6-5-7]-tricyclic Indoles in excellent yields. The reaction is completely regioselective and offers high levels of syn diastereoselectivity. The reaction Is also seen to be sensitive to substrate structure and catalyst.
Original languageEnglish
Pages (from-to)1175-1178
Number of pages4
JournalOrganic Letters
Volume11
Issue number5
Early online date11 Feb 2009
DOIs
Publication statusPublished - 5 Mar 2009

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Indoles
alkylation
indoles
Alkylation
Ketones
ketones
vehicles
Friedel-Crafts reaction
Friedel-Craft reaction
Catalysts
Substrates
catalysts
1,3-butadiene

Cite this

Stereoselective double Friedel-Crafts alkylation of indoles with divinyl ketones. / Silvanus, Andrew C; Heffernan, Stephen J; Liptrot, D J; Kociok-Kohn, Gabriele; Andrews, B I; Carbery, David R.

In: Organic Letters, Vol. 11, No. 5, 05.03.2009, p. 1175-1178.

Research output: Contribution to journalArticle

Silvanus, Andrew C ; Heffernan, Stephen J ; Liptrot, D J ; Kociok-Kohn, Gabriele ; Andrews, B I ; Carbery, David R. / Stereoselective double Friedel-Crafts alkylation of indoles with divinyl ketones. In: Organic Letters. 2009 ; Vol. 11, No. 5. pp. 1175-1178.
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