Enantioselective Iridium-Catalyzed Hydrogenation of 3,4-Disubstituted Isoquinolines

Enantioselective Iridium-Catalyzed Hydrogenation of 3,4-Disubstituted Isoquinolines

Reining in the outliers: An efficient approach for enantioselective hydrogenation of 3,4‐disubstituted isoquinolines was successfully developed. When isoquinolines are treated with [Ir(cod)Cl]2/(R)‐synphos in the presence of 1‐bromo‐3‐chloro‐5,5‐dimethyl‐hydantoin (BCDMH), the chiral 3,4‐disubstitut...

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Veröffentlicht in:Angewandte Chemie International Edition 2012-08, Vol.51 (33), p.8286-8289
Hauptverfasser: Shi, Lei, Ye, Zhi-Shi, Cao, Liang-Liang, Guo, Ran-Ning, Hu, Yue, Zhou, Yong-Gui
Format: Artikel
Sprache:eng
Schlagworte:
1,2,3,4‐tetrahydroisoquinoline
4-tetrahydroisoquinoline
asymmetric catalysis
Catalysis
Derivatives
Hydrogenation
Iridium
Iridium - chemistry
isoquinoline
Isoquinolines - chemical synthesis
Isoquinolines - chemistry
Molecular Structure
Organometallic Compounds - chemistry
Stereoisomerism
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Zusammenfassung:Reining in the outliers: An efficient approach for enantioselective hydrogenation of 3,4‐disubstituted isoquinolines was successfully developed. When isoquinolines are treated with [Ir(cod)Cl]2/(R)‐synphos in the presence of 1‐bromo‐3‐chloro‐5,5‐dimethyl‐hydantoin (BCDMH), the chiral 3,4‐disubstituted tetrahydroisoquinoline derivatives are obtained with ee values as high as 96 % (see scheme; cod=1,5‐cyclooctadiene).
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201203647