Regio- and Stereoselective Synthesis of 1,2,3-Trisubstituted Indanes from Diarylmethanols and Allylamides through Iron(III) Chloride Hexahydrate

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• 作者：Yali Li ; Lingjuan Zhang ; Zongyao Zhang ; Jianbin Xu ; Yixiao Pan ; Conghui Xu ; Lingxian Liu ; Zengguang Li ; Zhiyong Yu ; Huanrong Li and Lijin Xu
• 刊名：Advanced Synthesis & Catalysis
• 出版年：2016
• 出版时间：June 30, 2016
• 年：2016
• 卷：358
• 期：13
• 页码：2148-2155
• 全文大小：992K
• ISSN：1615-4169

文摘

An efficient method for the highly regio- and stereoselective synthesis of 1,2,3-trisubstituted indanes from diarylmethanols and allylamides through iron(III) chloride hexahydrate-catalyzed intermolecular [3+2] cycloaddition reaction is reported. A range of 1,2,3-trisubstituted indanes were prepared in good to excellent yields with excellent stereoselectivities for various combinations of diarylmethanols and allylamides. The choice of solvent is critical to the catalysis. Mechanistic studies indicated that the generation of a benzylic cation is involved in this catalytic process, and the reaction proceeds via the initial formation of diarylmethyl ethers. This reaction features ready availability of the starting materials, high level of functional tolerance and simple experimental operation.