Asymmetric Hydrogenation of Protected Allylic Amines

A general method for the enantioselective hydrogenation of protected allylic amine derivatives is described. This procedure relies on the generation of a cationic ruthenium complex with the axially chiral ligand (−)-TMBTP. The utility is highlighted by the highly enantioselective hydrogenation of a...

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Bibliographic Details
Published in:Organic letters 2010-09, Vol.12 (18), p.4201-4203
Main Authors: Steinhuebel, Dietrich P, Krska, Shane W, Alorati, Anthony, Baxter, Jenny M, Belyk, Kevin, Bishop, Brian, Palucki, Michael, Sun, Yongkui, Davies, Ian W
Format: Article
Language:English
Subjects:
Allyl Compounds - chemistry
Amines - chemistry
Azepines - chemical synthesis
Caprolactam - chemical synthesis
Catalysis
Hydrogenation
Imidazoles - chemical synthesis
Molecular Structure
Stereoisomerism
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Summary:A general method for the enantioselective hydrogenation of protected allylic amine derivatives is described. This procedure relies on the generation of a cationic ruthenium complex with the axially chiral ligand (−)-TMBTP. The utility is highlighted by the highly enantioselective hydrogenation of a diene substrate that can then be elaborated to prepare Telcagepant, a compound currently in Phase III clinical trials. The scope of the hydrogenation reaction was studied, and a variety of substituted allylic amine derivatives could be hydrogenated with enantiomeric ratios of 92:8 or higher.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol101804e