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- Title
Aryloxide-Facilitated Catalyst Turnover in Enantioselective α,β-Unsaturated Acyl Ammonium Catalysis.
- Authors
Matviitsuk, Anastassia; Greenhalgh, Mark D.; Antúnez, Diego‐Javier Barrios; Slawin, Alexandra M. Z.; Smith, Andrew D.
- Abstract
A new general concept for α,β-unsaturated acyl ammonium catalysis is reported that uses p-nitrophenoxide release from an α,β-unsaturated p-nitrophenyl ester substrate to facilitate catalyst turnover. This method was used for the enantioselective isothiourea-catalyzed Michael addition of nitroalkanes to α,β-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 α,β-unsaturated p-nitrophenyl ester, and a recently reported variable-time normalization kinetic analysis method was used to delineate the complex reaction kinetics.
- Subjects
ENANTIOSELECTIVE catalysis; MICHAEL reaction; NITROALKANES; ACYLATION; ORGANOCATALYSIS
- Publication
Angewandte Chemie, 2017, Vol 129, Issue 40, p12450
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201706402