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J Am Chem Soc. 2008 Jul 23;130(29):9246-7. doi: 10.1021/ja8041542. Epub 2008 Jun 27.

A Brønsted acid catalyst for the enantioselective protonation reaction.

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  • 1Department of Chemistry, University of Chicago, 5735 South Ellis Avenue, Chicago, Illinois 60637, USA.


A highly reactive and robust chiral Brønsted acid catalyst, chiral N-triflyl thiophosphoramide, was developed. The first metal-free Brønsted acid catalyzed enantioselective protonation reaction of silyl enol ethers was demonstrated using this chiral Brønsted acid catalyst. The catalyst loading could be reduced to 0.05 mol % without any deleterious effect on the enantioselectivity.

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