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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 34, 2004 - Issue 4
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Original Articles

A Formal [3 + 2] Alkene Addition to Benzhydrol Cations. A Practical and Mild Methodology for the Synthesis of Substituted 1‐Arylindanes and Related Compounds

Beatriz Lantaño Departamento de Química Orgánica, Facultad de Farmacia y Bioquímica, Universidad de Buenos Aires, Junín 956 (1113), Buenos Aires, Argentina
,
Jose M. Aguirre Departamento de Ciencias Básicas, Universidad Nacional de Luján, Luján, Argentina
,
Liliana Finkielsztein Departamento de Química Orgánica, Facultad de Farmacia y Bioquímica, Universidad de Buenos Aires, Junín 956 (1113), Buenos Aires, Argentina
,
Elba N. Alesso Departamento de Química Orgánica, Facultad de Farmacia y Bioquímica, Universidad de Buenos Aires, Junín 956 (1113), Buenos Aires, Argentina
,
Ernesto Brunet Departamento de Química Orgánica, Universidad Autónoma de Madrid, Cantoblanco, Madrid, España
&
Graciela Y. Moltrasio Departamento de Química Orgánica, Facultad de Farmacia y Bioquímica, Universidad de Buenos Aires, Junín 956 (1113), Buenos Aires, ArgentinaCorrespondence[email protected]
Pages 625-641 | Received 14 Aug 2003, Published online: 16 Aug 2006
 
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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.

Acknowledgments

This work was supported by grants from the Consejo Nacional de Investigaciones Cientifícas y Técnicas (CONICET) and Universidad de Buenos Aires.

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