Indium(0)-Catalyzed Allylations of Ketones in Water

Significance

Though In(III)-catalyzed C-C bond formations are common, this report highlights the first In(0)-catalyzed C-C bond-forming process. Ketone allylations can be achieved using allyl­boronates in the presence of as little as 3 mol% of In(0). Interestingly, aqueous medium is required and the reaction is performed solely in water. Using α-methylallylboronate gives exclusively α-addition to the ketones in good yields and moderate syn/anti selectivity. A preliminary result for the asymmetric version of this reaction is reported using a chiral bis(oxazoline) ligand.