A Highly Enantioselective Access to Tetrahydroisoquinoline and β-Carboline Alkaloids with Simple Noyori-Type Catalysts in Aqueous Media

Silver enhancement: A very convenient modified protocol for the enantioselective transfer hydrogenation of dihydroisoquinoline skeletons under aqueous conditions is reported. Unmodified Noyori ligands can be used and the activity of the catalyst is greatly enhanced with silver additives (see scheme)...

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Veröffentlicht in:Chemistry : a European journal 2009-12, Vol.15 (47), p.12963-12967
Hauptverfasser: Evanno, Laurent, Ormala, Joel, Pihko, Petri M.
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creator Evanno, Laurent
Ormala, Joel
Pihko, Petri M.
description Silver enhancement: A very convenient modified protocol for the enantioselective transfer hydrogenation of dihydroisoquinoline skeletons under aqueous conditions is reported. Unmodified Noyori ligands can be used and the activity of the catalyst is greatly enhanced with silver additives (see scheme). The protocol was used in a very short synthesis of the alkaloids (S)‐harmicine and (S)‐crispine.
doi_str_mv 10.1002/chem.200902289
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source Wiley Online Library Journals Frontfile Complete
subjects alkaloids
asymmetric synthesis
catalysis
imines
lanthanides
transfer hydrogenation
title A Highly Enantioselective Access to Tetrahydroisoquinoline and β-Carboline Alkaloids with Simple Noyori-Type Catalysts in Aqueous Media
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