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Issue 27, 2013
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Enantioselective synthesis of almorexant via iridium-catalysed intramolecular allylic amidation

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Abstract

An enantioselective synthesis of almorexant, a potent antagonist of human orexin receptors, is presented. The chiral tetrahydroisoquinoline core structure was prepared via iridium-catalysed asymmetric intramolecular allylic amidation. Further key catalytic steps of the synthesis include an oxidative Heck reaction at room temperature and a hydrazine-mediated organocatalysed reduction.

Graphical abstract: Enantioselective synthesis of almorexant via iridium-catalysed intramolecular allylic amidation

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Publication details

The article was received on 03 Apr 2013, accepted on 17 May 2013 and first published on 20 May 2013


Article type: Paper
DOI: 10.1039/C3OB40655E
Org. Biomol. Chem., 2013,11, 4521-4525

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    Enantioselective synthesis of almorexant via iridium-catalysed intramolecular allylic amidation

    M. Fañanás-Mastral, J. F. Teichert, J. A. Fernández-Salas, D. Heijnen and B. L. Feringa, Org. Biomol. Chem., 2013, 11, 4521
    DOI: 10.1039/C3OB40655E

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