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2-Phospha[3]ferrocenophanes with Planar Chirality: Synthesis and Use in Enantioselective Organocatalytic [3 + 2] Cyclizations

Arnaud Voituriez, Armen Panossian, Nicolas Fleury-Brégeot, Pascal Retailleau and Angela Marinetti*

*Institut de Chimie des Substances Naturelles, CNRS UPR 2301 - 1, av. de la Terrasse, 91198 Gif-sur-Yvette, France, Email: angela.marinettiicsn.cnrs-gif.fr

A. Voituriez, A. Panossian, N. Fleury-Brégeot, P. Retailleau, A. Marinetti, J. Am. Chem. Soc., 2008, 130, 14030-14031.

DOI: 10.1021/ja806060a (free Supporting Information)



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Abstract

A P-cyclohexyl substituted ferrocenophane catalyst affords high levels of asymmetric induction in the organocatalytic [3 + 2] annulation reaction between allenes and electron-poor olefins.

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Mechanism of nucleophilic catalysis (see C. Zhang, X. Lu, J. Org. Chem., 1995, 2906.)



Key Words

1,3-dipolar cycloaddition, organocatalysis, cyclopentenes, unsaturated compounds


ID: J48-Y2008-3010