Regio‐ and Stereoselective Synthesis of 1, 2, 3‐Trisubstituted Indanes from Diarylmethanols and Allylamides through Iron(III) Chloride Hexahydrate. Issue 13 (16th June 2016)

• Record Type: Journal Article
• Authors: Li, Yali; Zhang, Lingjuan; Zhang, Zongyao; Xu, Jianbin; Pan, Yixiao; Xu, Conghui; Liu, Lingxian; Li, Zengguang; Yu, Zhiyong; Li, Huanrong; Xu, Lijin
• Is Part Of: Advanced synthesis & catalysis. Volume 358:Issue 13(2016)
• Page Start: 2148
• Page End: 2155
• Publication Date: 2016-06-16
• Subjects: allylamides -- diarylmethanol -- indane -- iron catalyst -- stereoselectivity; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.201600165
• Languages: English
• ISSNs: 1615-4150

Abstract

Abstract: 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. Abstract :