A Reusable TNF-Tagged Chiral Bis(oxazoline)–Copper Catalyst for Diels–
Alder Transformations

Dorian Didier; Emmanuelle Schulz

doi:10.1055/s-0031-1290918

Synlett, Table of Contents

Synlett 2012; 23(9): 1309-1314
DOI: 10.1055/s-0031-1290918

letter

A Reusable TNF-Tagged Chiral Bis(oxazoline)–Copper Catalyst for Diels– Alder Transformations

Dorian Didier

^aEquipe de Catalyse Moléculaire, Univ Paris-Sud, ICMMO, UMR 8182, Orsay 91405, France

,

Emmanuelle Schulz*

^aEquipe de Catalyse Moléculaire, Univ Paris-Sud, ICMMO, UMR 8182, Orsay 91405, France

^bCNRS, Orsay 91405, France, Fax: +33(1)69154680 Email: emmanuelle.schulz@u-psud.fr

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Abstract

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Abstract

A chiral bis(oxazoline) ligand, substituted on the methylene bridge by a covalent link to an electron-deficient moiety (2,4,7-trinitrofluoren-9-one, TNF), is a useful ligand associated to copper(II) salts to promote enantioselective Diels–Alder reactions between N-acyloxazolidinones and cyclopentadiene. Owing to different solubility properties, the corresponding catalyst was precipitated by pentane addition after reaction completion and was easily recovered by filtration. It was successfully reused in up to 20 successive catalytic cycles for the formation of the targeted products with no loss of either the activity or the enantioselectivity along with the recycling.

Key words

asymmetric catalysis - charge transfer complexes - copper - Diels–Alder reaction - catalyst recovery

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References

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