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Issue 76, 2013
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An efficient route to chiral N-heterocycles bearing a C–F stereogenic center via asymmetric hydrogenation of fluorinated isoquinolines

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Abstract

An efficient iridium-catalyzed asymmetric hydrogenation of the fluorinated isoquinoline derivatives has been successfully developed for the synthesis of chiral fluorinated tetrahydroisoquinoline derivatives with up to 93% ee. This methodology features the use of a hydrochloride salt as well as a catalytic amount of halogenated hydantoin which were vital for the reactivity, enantioselectivity, and inhibition of the hydrodefluorination pathway.

Graphical abstract: An efficient route to chiral N-heterocycles bearing a C–F stereogenic center via asymmetric hydrogenation of fluorinated isoquinolines

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Publication details

The article was received on 15 Jul 2013, accepted on 22 Jul 2013 and first published on 22 Jul 2013


Article type: Communication
DOI: 10.1039/C3CC45341C
Citation: Chem. Commun., 2013,49, 8537-8539
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    An efficient route to chiral N-heterocycles bearing a C–F stereogenic center via asymmetric hydrogenation of fluorinated isoquinolines

    R. Guo, X. Cai, L. Shi, Z. Ye, M. Chen and Y. Zhou, Chem. Commun., 2013, 49, 8537
    DOI: 10.1039/C3CC45341C

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