4.3 Article

A formal [3+2] alkene addition to benzhydrol cations.: A practical and mild methodology for the synthesis of substituted 1-arylindanes and related compounds

Journal

SYNTHETIC COMMUNICATIONS
Volume 34, Issue 4, Pages 625-641

Publisher

TAYLOR & FRANCIS INC
DOI: 10.1081/SCC-120027710

Keywords

styrenes; stilbenes indanes; cycloadditions

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We report the single step synthesis of several 1-arylindanes in good yield via a formal [3 + 2] atom cycloaddition. The success of this formal cycloaddition relies on the Lewis acid activation of a bibenzylic alcohol in the presence of an alkene. The cation generated from the alcohol can be trapped by the alkene to afford a new benzylic cation which can then undergoes cyclization leading to 1-arylindanes with three stereogenic centres.

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