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Synlett 2016; 27(03): 320-330
DOI: 10.1055/s-0035-1560801
DOI: 10.1055/s-0035-1560801
synpacts
Nucleophilic Capture of Unsymmetrical Oxyallyl Cations with Indoles under Mild Brønsted Acid Catalysis
Further Information
Publication History
Received: 02 August 2015
Accepted after revision: 25 September 2015
Publication Date:
07 December 2015 (online)
![](https://www.thieme-connect.de/media/synlett/201603/lookinside/thumbnails/st-2015-p0607-sp_10-1055_s-0035-1560801-1.jpg)
Abstract
We recently reported a new synthetic method in our laboratory concerning the control of regioselectivity in the addition of nucleophiles, such as indoles, to unsymmetrical oxyallyl cations. These reactive intermediates were readily generated upon ionization of the corresponding α-hydroxy enol ether precursors under catalytic, mild Brønsted acid. Results from our expansive scope of substrate studies revealed that regioselectivity in this reaction could be regulated upon protection of the oxygen atom in the oxyallyl cation moiety as well as modulation of the stereoelectronic effects in the participating α vs. α′ substituents.
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