Asymmetric Hydrogenation of Protected Allylic Amines

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• 作者：Dietrich P. Steinhuebel ; Shane W. Krska ; Anthony Alorati ; Jenny M. Baxter ; Kevin Belyk ; Brian Bishop ; Michael Palucki ; Yongkui Sun ; Ian W. Davies
• 刊名：Organic Letters
• 出版年：2010
• 出版时间：September 17, 2010
• 年：2010
• 卷：12
• 期：18
• 页码：4201-4203
• 全文大小：171K
• 年卷期：v.12,no.18(September 17, 2010)
• ISSN：1523-7052

文摘

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.