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Asymmetrie iminium ion catalysis with a novel bifunctional primary amine thiourea: Controlling adjacent quaternary and tertiary stereocenters
The development of a new bifunctional chiral primary amine thiourea catalyst and its application in the first asymmetric conjugate addition of oxindoles to enales was described. The reaction between 3-methyl oxindole and cinnamaldehyde, a combination of simple and readily available starting materials that targets in organic synthesis, was selected. The poor catalytic performance and the very low selectivity observed suggest a critical role of the thiourea moiety during the steroselective C-C bond-forming step. It is also found that by using 50% of benzoic acid, the catalyst loading is reduced to 10%, while still maintaining high diastero and enantiocontrol, and significant reactivity. The best diasterocontrol is observed for enals that have a naphthyl beta substituted and by using oxindole that has a benzyl substitute.
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Reference£º
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI