Metal-Free Cycloetherification by in Situ Generated P-Stereogenic α-Diazanium Intermediates: A Convergent Synthesis of Enantiomerically Pure Dihydrobenzooxaphospholes

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• 作者：Shi-Guang Li ; Zhengxu S. Han ; Peter Viereck ; Heewon Lee ; Dmitry Kurouski ; Chris H. Senanayake ; Youla S. Tsantrizos
• 刊名：Organic Letters
• 出版年：2017
• 出版时间：February 17, 2017
• 年：2017
• 卷：19
• 期：4
• 页码：894-897
• 全文大小：425K
• ISSN：1523-7052

文摘

A metal-free tandem reaction, initiated by the generation of a diazonium cation and followed by cycloetherification, was developed. Acid-promoted de-tert-butylation of N-nitroso N-tert-butylamine was used to generate a diazonium cation in situ, demonstrating a new application of nitroso chemistry. This reaction was employed in the synthesis of substituted benzofuran-3(2H)-ones and dihydrobenzo[d][1,3]oxaphosphole 3-oxides.