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Asymmetric Counteranion-Directed Lewis Acid Catalysis with α,β-Unsaturated Esters


Gatzenmeier,  Tim
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Gatzenmeier, T. (2018). Asymmetric Counteranion-Directed Lewis Acid Catalysis with α,β-Unsaturated Esters. PhD Thesis, Universität zu Köln, Köln.

Cite as: http://hdl.handle.net/21.11116/0000-0002-B636-4
The fundamental substrate class of α,β-unsaturated esters offers extraordinary synthetic potential for carbon-carbon bond forming reactions, such as cycloadditions and conjugate additions, however is rarely applied in asymmetric catalysis due to its relatively low reactivity. By expanding the concept of silylium-ACDC to non-silicon transfer reactions (catalytic in silicon), the introduction of chiral C–H acids into asymmetric catalysis and the identification of two distinct families of imidodiphosphorimidates (IDPi) catalysts, we could report unprecedented highly enantio- and diastereoselective Diels–Alder and Mukaiyama– Michael reactions of simple α,β-unsaturated methyl esters. The developed extremely active chiral Lewis acids represent the most efficient catalysts for asymmetric Diels–Alder reactions of α,β-unsaturated esters to date while tolerating a very broad scope on a variable scale with catalyst loadings as low as 0.1 mol%.