Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 56, Issue 40, Pages 12282-12287Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201706402
Keywords
aryloxides; isothiourea; kinetic analysis; Lewis base catalysis; -unsaturated ammonium compounds
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Funding
- European Research Council under the European Union [279850]
- EPSRC [EP/J018139/1]
- Royal Society for a Wolfson Research Merit Award
- Engineering and Physical Sciences Research Council [EP/J018139/1] Funding Source: researchfish
- EPSRC [EP/J018139/1] Funding Source: UKRI
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A new general concept for ,-unsaturated acyl ammonium catalysis is reported that uses p-nitrophenoxide release from an ,-unsaturated p-nitrophenyl ester substrate to facilitate catalyst turnover. This method was used for the enantioselective isothiourea-catalyzed Michael addition of nitroalkanes to ,-unsaturated p-nitrophenyl esters in generally good yield and with excellent enantioselectivity (27 examples, up to 79% yield, 99:1 er). Mechanistic studies identified rapid and reversible catalyst acylation by the ,-unsaturated p-nitrophenyl ester, and a recently reported variable-time normalization kinetic analysis method was used to delineate the complex reaction kinetics.
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