Cascade Cycloadditions for the Synthesis of Perylenes

doi:10.1055/s-0030-1258730

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Synfacts 2010(11): 1237-1237
DOI: 10.1055/s-0030-1258730

Synthesis of Materials and Unnatural Products

Cascade Cycloadditions for the Synthesis of Perylenes

Contributor(s): Timothy M. Swager, Shuang Liu
A. Criado, D. Peña*, A. Cobas, E. Guitián*
Universidade de Santiago de Compostela, Spain

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Publication History

Publication Date:
21 October 2010 (online)

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Significance

Perylene derivatives were prepared by cascade [4+2] cycloadditions between 1,8-difurylnaphthalene and arynes. The double Diels-Alder reaction proceeds in a highly stereoselective fashion and only the exo,exo-diastereomer (3a-c) is formed as confirmed by X-ray crystallographic studies.