Org Lett. 2010 Sep 17;12(18):4201-3.

Asymmetric hydrogenation of protected allylic amines.

Steinhuebel DP, Krska SW, Alorati A, Baxter JM, Belyk K, Bishop B, Palucki M, Sun Y, Davies IW.

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Department 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.

PMID:: 20735080; [PubMed - indexed for MEDLINE]

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