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

Authors
  • Ayala, Caitlan E
  • Dange, Nitin S
  • Fronczek, Frank R
  • Kartika, Rendy
Type
Published Article
Journal
Angewandte Chemie International Edition in English
Publisher
Wiley (John Wiley & Sons)
Publication Date
Apr 07, 2015
Volume
54
Issue
15
Pages
4641–4645
Identifiers
DOI: 10.1002/anie.201409758
PMID: 25694101
Source
Medline
Keywords
License
Unknown

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.

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