Enantioselective Copper-Catalyzed Propargylic Amination

A proper copper catalyst with a chiral pyridine‐2,6‐bisoxazoline (pybox) ligand was used to convert a variety of propargylic acetates with aromatic side chains (R=Ar) into their amine counterparts in high yield and with good selectivity (up to 88 % ee). The resulting chiral propargylic amines can be...

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Bibliographic Details
Published in:Angewandte Chemie (International ed.) 2008-05, Vol.47 (20), p.3777-3780
Main Authors: Detz, Remko J, Delville, Mariëlle M.E, Hiemstra, Henk, van Maarseveen, Jan H
Format: Article
Language:English
Subjects:
Amination
asymmetric catalysis
Catalysis
Copper - chemistry
N ligands
P,N ligands
Pargyline - analogs & derivatives
Pargyline - chemical synthesis
propargylic amines
Propylamines - chemical synthesis
pybox ligands
Stereoisomerism
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Summary:A proper copper catalyst with a chiral pyridine‐2,6‐bisoxazoline (pybox) ligand was used to convert a variety of propargylic acetates with aromatic side chains (R=Ar) into their amine counterparts in high yield and with good selectivity (up to 88 % ee). The resulting chiral propargylic amines can be elaborated further into P,N ligands (see scheme; DIPEA=diisopropylethylamine).
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200705264