Angewandte Chemie. International edition in English 2015-04-07

Brønsted acid catalyzed α'-functionalization of silylenol ethers with indoles.

Caitlan E Ayala, Nitin S Dange, Frank R Fronczek, Rendy Kartika

Index: Angew. Chem. Int. Ed. Engl. 54(15) , 4641-5, (2015)

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Abstract

A new method which enables carbon-carbon bond formation at the α'-position of silylenol ethers by using catalytic amounts of pyridinium triflate is reported. This chemistry successfully produces, structurally challenging, highly substituted indole-containing silylenol ethers in excellent yields with complete regiocontrol, presumably through silyloxyallyl cation intermediates. Despite the use of Brønsted acid, the silylenol ether moiety does not undergo protodesilylation, thus underscoring the very mild reaction conditions. © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.