Elsevier

Tetrahedron Letters

Volume 52, Issue 51, 21 December 2011, Pages 6978-6981
Tetrahedron Letters

Micellar-driven substrate selectivity in Cr(salen)Cl catalytic Diels–Alder reaction in water

https://doi.org/10.1016/j.tetlet.2011.10.088Get rights and content

Abstract

A 3.5 increase in catalytic activity was observed in the Cr(III) (salen)Cl 3 catalyzed Diels–Alder reaction between cyclopentadiene 1 with the longer trans-2-decenal 2g compared to the shorter trans-2-butenal 2a dienophile under aqueous micellar conditions, while in chloroform the two substrates react with comparable activities.

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Acknowledgments

The authors thank MIUR, Università Ca’ Foscari di Venezia and ‘Consorzio Interuniversitario Nazionale per la Scienza e Tecnologia dei Materiali’ for financial support. L. Sperni for GC–MS analysis is gratefully acknowledged.

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