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Synfacts 2008(9): 0991-0991
DOI: 10.1055/s-2008-1078666
DOI: 10.1055/s-2008-1078666
Organo- and Biocatalysis
© Georg Thieme Verlag
Stuttgart ˙ New York
A New Chiral Brønsted Acid Catalyst
C. H. Cheon, H. Yamamoto*
The University of Chicago, USA
Further Information
Publication History
Publication Date:
22 August 2008 (online)

Significance
Yamamoto and Cheon present the new designer chiral Brønsted acid catalyst 1 and its application to the enantioselective protonation of silyl enol ethers. Several new catalysts were tested and it turned out that N-triflyl thiophosphoramides were the most effective catalysts. Using catalyst 1, the catalyst loading can be reduced down to 0.05 mol% without any significant loss in enantioselectivity although the reaction time is longer. A plausible two-step mechanism is suggested.