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A Formal [3 + 2] Alkene Addition to Benzhydrol Cations. A Practical and Mild Methodology for the Synthesis of Substituted 1‐Arylindanes and Related Compounds
23
Citations
11
References
2004
Year
Bibenzylic AlcoholEnantioselective SynthesisEngineeringHeterocyclicAlkene MetathesisNatural SciencesDiversity-oriented SynthesisOrganic ChemistryLewis Acid ActivationChemistrySingle Step SynthesisHeterocycle ChemistryRelated CompoundsSynthetic ChemistryBiomolecular EngineeringMild MethodologySubstituted 1‐Arylindanes
Abstract 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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