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

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.
Format: Artikel
Sprache:eng
Schlagworte:
alkaloids
asymmetric synthesis
catalysis
imines
lanthanides
transfer hydrogenation
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Zusammenfassung: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.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.200902289