Development of an Enantioselective Hydrogenation Route to (S)-1-(2-(Methylsulfonyl)pyridin-4-yl)propan-1-amine

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• 作者：Jonathan T. Reeves ; Zhulin Tan ; Diana C. Reeves ; Jinhua J. Song ; Zhengxu S. Han ; Yibo Xu ; Wenjun Tang ; Bing-Shiou Yang ; Hossein Razavi ; Christian Harcken ; Daniel Kuzmich ; Paige E. Mahaney ; Heewon Lee ; Carl A. Busacca ; Chris H. Senanayake
• 刊名：Organic Process Research & Development
• 出版年：2014
• 出版时间：July 18, 2014
• 年：2014
• 卷：18
• 期：7
• 页码：904-911
• 全文大小：348K
• ISSN：1520-586X

文摘

A highly enantioselective enamide hydrogenation route to the title amine was developed. Highlights of the synthesis include an efficient two-step synthesis of a 2-sulfonyl 4-pyridyl ethyl ketone, a simple enamide synthesis by direct condensation of propionamide with a ketone, catalytic asymmetric enamide hydrogenation employing the in-house-developed ligand MeO-BIBOP, and a mild epimerization-free deprotection of a propionamide using Koenig鈥檚 procedure.