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Updated: Jun 9, 2026

Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Asymmetric hydrogenation of protected allylic amines
Dietrich P Steinhuebel1, Shane W Krska, Anthony Alorati
1Department of Process Research, Merck & Co. Inc., PO Box 2000, Rahway, New Jersey 07065, USA. dietrich_steinhuebel@merck.com
Abstract:
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.
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