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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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Article information


Submitted
03 Apr 2013
Accepted
17 May 2013
First published
20 May 2013

Org. Biomol. Chem., 2013,11, 4521-4525
Article type
Paper

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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