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Issue 8, 2018
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Efficient access to chiral benzo[c]chromenes via asymmetric transfer hydrogenation of ketals

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Abstract

A highly enantioselective synthetic method to access chiral α-substituted 6H-benzo[c]chromenes through chiral imidodiphosphoric acid-catalyzed asymmetric transfer hydrogenation of the corresponding ketals has been established. The substituent patterns at the α-position proved to be unsusceptible to the asymmetric catalysis system, with diverse hybrid substituents including aryl and vinyl, alkynyl, and alkyl moieties that were well tolerated. In addition, the generality of the method was further demonstrated by application to 1H-isochromene-based ketals, offering chiral α-aryl and -alkyl 1H-isochromenes in excellent ee.

Graphical abstract: Efficient access to chiral benzo[c]chromenes via asymmetric transfer hydrogenation of ketals

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Publication details

The article was received on 28 Jan 2018, accepted on 26 Feb 2018 and first published on 08 Mar 2018


Article type: Research Article
DOI: 10.1039/C8QO00096D
Citation: Org. Chem. Front., 2018,5, 1280-1283
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    Efficient access to chiral benzo[c]chromenes via asymmetric transfer hydrogenation of ketals

    Y. Li, M. Wan, S. Sun, Z. Fu, H. Huang and L. Liu, Org. Chem. Front., 2018, 5, 1280
    DOI: 10.1039/C8QO00096D

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