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Merged Gold/Metal and Gold/Organo-Catalysis:
Reactions catalyzed by two different catalysts at the same time can provide access to the reactivity and selectivity of the reaction which is otherwise not possible with a single catalyst alone (Our reviews: Org. Biomol. Chem., 2012, 10, 211; Org. Biomol. Chem., 2015, 13, 8116; Angew. Chem., Int. Ed., 2011, 50, 1759 and ACS Catal., 2020, 10, 3462). As far as asymmetric catalysis is concerned, this chemistry is very appealing for Au(I) catalysis, given the difficulties of transferring chiral information from a ligand disposed at 180º from the substrate (Our review: Chem. Commun., 2014, 50, 15124). Essential for the success of the reaction is the role of gold phosphate LAuB, generated in situ from LAuMe and chiral Brønsted acid (B*–H) with the extrusion of methane. Here, the counter-ion (B*¯) has been shown to play a crucial role in controlling the reactivities and enantioselectivities of the process. Some of the reactions are schematically described below.
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While experimenting with gold-phosphates, which are the putative active catalysts in Au(I)/HB* co-operative catalyst system, our group has been able to develop the organocatalytic asymmetric 1,3-alkyl shift in alkyl aryl ethers using a chiral Brønsted acid catalyst for the synthesis of chiral 3,3'-diaryloxindoles.
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