Abstract
The asymmetric Michael addition of Meldrum’s acid to nitroalkenes was studied using a novel type of Cinchona alkaloid-based bifunctional thiourea organocatalyst. The functionality of the thiourea catalysts was also probed by preparing and testing thiourea-N-methylated analogues of the well-known bis-(3,5-trifluoromethyl)phenyl-substituted catalyst.
Highlights
Enantioselective carbon-carbon bond formation is one of the lasting challenges in organic chemistry
Asymmetric organocatalysis is in high demand and the subject of rigorous study.[1]
Among the several promising examples are Cinchona-alkaloid derived thiourea catalysts that have been found to be effective in a wide range of reactions
Summary
Enantioselective carbon-carbon bond formation is one of the lasting challenges in organic chemistry. A recent report suggested that the bicoordinating ability of the H-bond donor site is not completely essential; according to a study by Lu,[6] the sulfonamide analogues of Cinchonaderived thiourea catalysts are quite able to catalyze the Michael reaction of β-ketoesters and nitroalkenes.
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