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Issue 2, 2016
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Chiral Brønsted acid-catalyzed enantioselective Friedel–Crafts reaction of 2-methoxyfuran with aliphatic ketimines generated in situ

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Abstract

An enantioselective Friedel–Crafts reaction with aliphatic ketimines generated in situ from hemiaminal ethers catalyzed by a chiral Brønsted acid was investigated. The reaction of 2-methoxyfuran with (thio)hydantoin-derived hemiaminal methyl ether proceeded under the influence of a chiral phosphoric acid catalyst to afford the corresponding adduct possessing a quaternary stereogenic center in high yield with high enantioselectivity. Theoretical studies were also conducted to clarify the mechanism of the stereochemical outcome and the major factors contributing to the efficient enantioselection.

Graphical abstract: Chiral Brønsted acid-catalyzed enantioselective Friedel–Crafts reaction of 2-methoxyfuran with aliphatic ketimines generated in situ

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Publication details

The article was received on 26 Aug 2015, accepted on 29 Oct 2015 and first published on 30 Oct 2015


Article type: Edge Article
DOI: 10.1039/C5SC03175C
Citation: Chem. Sci., 2016,7, 1057-1062
  • Open access: Creative Commons BY-NC license
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    Chiral Brønsted acid-catalyzed enantioselective Friedel–Crafts reaction of 2-methoxyfuran with aliphatic ketimines generated in situ

    A. Kondoh, Y. Ota, T. Komuro, F. Egawa, K. Kanomata and M. Terada, Chem. Sci., 2016, 7, 1057
    DOI: 10.1039/C5SC03175C

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