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Synthesis 2017; 49(14): 3137-3144
DOI: 10.1055/s-0036-1589004
DOI: 10.1055/s-0036-1589004
paper
Regioselective Domino Synthesis of 2-Alkylflavans via Hidden Brønsted Acid Catalysis
Gefördert durch: This study was supported by the Kyung Hee University Research Fund (KHU-20130575)Weitere Informationen
Publikationsverlauf
Received: 25. Januar 2017
Accepted after revision: 24. März 2017
Publikationsdatum:
25. April 2017 (online)
Abstract
A range of alkyl-substituted flavans, which are important structural elements in natural products and pharmaceutical molecules, were prepared by successive hidden Brønsted acid catalyzed domino reaction, intermolecular hydroarylation, and intramolecular hydroalkoxylation. 1,1-Disubstituted allenes were activated under mild acidic AgOTf/t-BuCl condition to initiate the regioselective Friedel–Crafts reaction with phenol derivatives, and the consecutive reaction triggered by the 6-endocyclization led to the formation of a new type of 2-alkylflavan. Mechanistic study of the reaction intermediates and control experiments support the catalytic pathway and advantage of hidden Brønsted acid catalysis.
Key words
2-alkylflavan - hidden Brønsted acid catalyst - arylallene - domino cyclocoupling - regioselectivitySupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1589004.
- Supporting Information
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