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  • Title: Stereoselective double Friedel-Crafts alkylation of indoles with divinyl ketones.
    Author: Silvanus AC, Heffernan SJ, Liptrot DJ, Kociok-Köhn G, Andrews BI, Carbery DR.
    Journal: Org Lett; 2009 Mar 05; 11(5):1175-8. PubMed ID: 19243195.
    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.
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