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

MPS-Authors
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Teller,  Henrik
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Flügge,  Susanne
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Goddard,  Richard
Service Department Lehmann (EMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Fürstner,  Alois
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Teller, H., Flügge, S., Goddard, R., & Fürstner, A. (2010). Enantioselective Gold Catalysis: Opportunities Provided by Monodentate Phosphoramidite Ligands with an Acyclic TADDOL Backbone. Angewandte Chemie, International Edition, 49(11), 1949-1953. doi:10.1002/anie.200906550.


Cite as: http://hdl.handle.net/11858/00-001M-0000-000F-8D9F-D
Abstract
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.