Highly Enantioselective Iridium-Catalyzed Hydrogenation of 2‑Aryl Allyl Phthalimides

Highly Enantioselective Iridium-Catalyzed Hydrogenation of 2‑Aryl Allyl Phthalimides

The iridium-catalyzed asymmetric hydrogenation of 2-aryl allyl phthalimides to afford enantioenriched β-aryl-β-methyl amines is presented. Recently developed Ir-MaxPHOX catalysts are used for this enantioselective transformation. The mild reaction conditions and the feasible removal of the phthalimi...

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Veröffentlicht in:Organic letters 2019-12, Vol.21 (23), p.9709-9713
Hauptverfasser: Cabré, Albert, Romagnoli, Elia, Martínez-Balart, Pol, Verdaguer, Xavier, Riera, Antoni
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container_end_page 9713
container_issue 23
container_start_page 9709
container_title Organic letters
container_volume 21
creator Cabré, Albert
Romagnoli, Elia
Martínez-Balart, Pol
Verdaguer, Xavier
Riera, Antoni
description The iridium-catalyzed asymmetric hydrogenation of 2-aryl allyl phthalimides to afford enantioenriched β-aryl-β-methyl amines is presented. Recently developed Ir-MaxPHOX catalysts are used for this enantioselective transformation. The mild reaction conditions and the feasible removal of the phthalimido group makes this catalytic method easily scalable and of great interest to afford chiral amines. The importance of this new methodology is exemplified by the formal synthesis of (R)-Lorcaserin, OTS514, and enantiomerically enriched 3-methyl indolines.
doi_str_mv 10.1021/acs.orglett.9b03865
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title Highly Enantioselective Iridium-Catalyzed Hydrogenation of 2‑Aryl Allyl Phthalimides
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