Synthesis of Allenamides by Copper-Catalyzed Coupling of Propargylic Bromides and Nitrogen Nucleophiles
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- 作者：Charles S. Demmer ; Emeline Benoit ; Gwilherm Evano
- 刊名：Organic Letters
- 出版年：2016
- 出版时间：March 18, 2016
- 年：2016
- 卷：18
- 期：6
- 页码：1438-1441
- 全文大小：370K
- ISSN：1523-7052
文摘
An efficient and general synthesis of allenamides derived from oxazolidinones and hydantoins is reported. Upon activation with a combination of a copper catalyst and a 2,2′-bipyridine derivative in the presence of an inorganic base, propargylic bromides were found to be suitable reagents for the direct allenylation of nitrogen nucleophiles by a formal copper-catalyzed SN2′ reaction. Besides the availability of the starting materials, notable features of this route to allenamides are its mild reaction conditions, the reaction being performed at room temperature in most cases, and its applicability to the preparation of mono-, di-, as well as trisubstituted allenamides.