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Synthesis 2017; 49(14): 3137-3144
DOI: 10.1055/s-0036-1589004
paper
© Georg Thieme Verlag Stuttgart · New York

Regioselective Domino Synthesis of 2-Alkylflavans via Hidden Brønsted Acid Catalysis

Ha Jeong Jin
Department of Applied Chemistry, Kyung Hee University, Yongin 17104, Korea   Email: ejkang24@khu.ac.kr
,
Jae Hyung Kim
Department of Applied Chemistry, Kyung Hee University, Yongin 17104, Korea   Email: ejkang24@khu.ac.kr
,
Eun Joo Kang*
Department of Applied Chemistry, Kyung Hee University, Yongin 17104, Korea   Email: ejkang24@khu.ac.kr
› Author AffiliationsSupported by: This study was supported by the Kyung Hee University Research Fund (KHU-20130575)
Further Information

Publication History

Received: 25 January 2017

Accepted after revision: 24 March 2017

Publication Date:
25 April 2017 (online)

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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 - regioselectivity

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1589004.
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