Enantioselective synthesis of almorexant via iridium-catalysed intramolecular allylic amidation

Martin Fananas Mastral; Johannes F. Teichert; Jose Antonio Fernandez-Salas; Dorus Heijnen; Ben L. Feringa

doi:10.1039/c3ob40655e

Enantioselective synthesis of almorexant via iridium-catalysed intramolecular allylic amidation

Martin Fananas Mastral, Johannes F. Teichert, Jose Antonio Fernandez-Salas, Dorus Heijnen, Ben L. Feringa

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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.

Original language	English
Pages (from-to)	4521-4525
Number of pages	5
Journal	Organic & Biomolecular Chemistry
Volume	11
Issue number	27
DOIs	https://doi.org/10.1039/c3ob40655e
Publication status	Published - 21-Jul-2013

Keywords

METATHESIS
HYDROGENATION
RACEMIZATION
SYSTEM
SLEEP

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title = "Enantioselective synthesis of almorexant via iridium-catalysed intramolecular allylic amidation",

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.",

keywords = "METATHESIS, HYDROGENATION, RACEMIZATION, SYSTEM, SLEEP",

author = "{Fananas Mastral}, Martin and Teichert, {Johannes F.} and Fernandez-Salas, {Jose Antonio} and Dorus Heijnen and Feringa, {Ben L.}",

year = "2013",

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doi = "10.1039/c3ob40655e",

language = "English",

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T1 - Enantioselective synthesis of almorexant via iridium-catalysed intramolecular allylic amidation

AU - Fananas Mastral, Martin

AU - Teichert, Johannes F.

AU - Fernandez-Salas, Jose Antonio

AU - Heijnen, Dorus

AU - Feringa, Ben L.

PY - 2013/7/21

Y1 - 2013/7/21

N2 - 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.

AB - 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.

KW - METATHESIS

KW - HYDROGENATION

KW - RACEMIZATION

KW - SYSTEM

KW - SLEEP

U2 - 10.1039/c3ob40655e

DO - 10.1039/c3ob40655e

M3 - Article

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VL - 11

SP - 4521

EP - 4525

JO - Organic & Biomolecular Chemistry

JF - Organic & Biomolecular Chemistry

IS - 27

ER -

Enantioselective synthesis of almorexant via iridium-catalysed intramolecular allylic amidation

Abstract

Keywords

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