Practical Asymmetric Synthesis of a Chiral Piperazinone Derivative

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• 作者：Mark McLaughlin ; Kevin Belyk ; Cheng-yi Chen ; Xin Linghu ; Jun Pan ; Gang Qian ; Robert A. Reamer ; Yingju Xu
• 刊名：Organic Process Research & Development
• 出版年：2013
• 出版时间：August 16, 2013
• 年：2013
• 卷：17
• 期：8
• 页码：1052-1060
• 全文大小：444K
• 年卷期：v.17,no.8(August 16, 2013)
• ISSN：1520-586X

文摘

A practical asymmetric route to a chiral piperazinone derivative, a fragment of MK-3207, is reported. The amine-bearing benzylic stereocenter is introduced via an asymmetric Pd-catalyzed hydrogenation of a cyclic sulfimidate in the presence of a chiral phosphine ligand. An efficient synthesis of the hydrogenation substrate is described, together with process development of the hydrogenation step and elaboration of the resulting cyclic sulfamate product to the desired piperazinone.