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Enantioselective Gold Catalysis: Opportunities Provided by Monodentate Phosphoramidite Ligands with an Acyclic TADDOL Backbone

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  • Generous financial support by the MPG and the Fonds der Chemischen Industrie (Kekulé fellowships to H.T. and S.F.) is gratefully acknowledged. We thank the NMR, X-ray, and Chromatography Departments of our Institute for their excellent support, and Umicore AG & Co KG, Hanau, for a gift of noble metal salts.

Abstract

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The tail makes the difference: Removing the isopropylidene acetal unit from well-known TADDOL ligands improved the performance of the derived phosphoramidite ligands in asymmetric gold catalysis (see scheme; Ts=4-toluenesulfonyl). X-ray crystallography showed that the binding pocket has an effective threefold symmetry, with through-space interactions between the arene rings of the ligand and the gold center.

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